COMPOUNDS AND THE USE THEREOF IN METATHESIS REACTIONS

• US 20170037069A1
• Filed: 04/09/2015
• Published: 02/09/2017
• Est. Priority Date: 04/11/2014
• Status: Active Grant

• Current Assignee: Verbio Se
• Original Assignee: Ximo AG (Verbio Se)
• Inventors: Toth, Florian, Frater, Georg, Ondi, Levente
• Granted Patent: US 10,106,566 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: B01J 2231/543 alkene metathesis
• CPC Class Codes: B01J 2531/64 Molybdenum
• CPC Class Codes: B01J 2531/66 Tungsten
• CPC Class Codes: B01J 31/2265 Carbenes or carbynes, i.e.(image)
• CPC Class Codes: C07C 11/02 Alkenes
• CPC Class Codes: C07C 15/12 Polycyclic non-condensed hydrocarbons
• CPC Class Codes: C07C 2531/22 Organic complexes
• CPC Class Codes: C07C 2601/10 the ring being unsaturated
• CPC Class Codes: C07C 6/04 at a carbon-to-carbon double bond
• CPC Class Codes: C07C 67/333 by isomerisation; by change of size of the carbon skeleton introduction or elimination of carboxyl groups C07C67/313, C07C67/32
• CPC Class Codes: C07C 67/475 by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
• CPC Class Codes: C07C 69/593 Dicarboxylic acid esters having only one carbon-to-carbon double bond
• CPC Class Codes: C07C 69/74 Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07D 321/00 Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
• CPC Class Codes: C07F 11/00 Compounds containing elements of Groups 6 or 16 of the Periodic Table

Abstract

The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula (I) wherein: M is a Group 6 metal atom; X is an oxygen atom, ═N—R⁵, ═N—N(R⁵)(R^5′) or ═N—O—R⁵, R⁵ and R^5′ independently being various substituents, such as aryl or heteroaryl, each optionally substituted; n is 0 or 1; R^z is a neutral ligand; R¹ is hydrogen or an organic substituent; R² is an aryl or heteroaryl group, each optionally substituted; R³ is an anionic ligand; and R⁴ is an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted.

Claims

1. A compound of Formula (I)

2. The compound of claim 1, wherein M is Mo or W.

3. The compound of claim 2, where M is Mo.

4. The compound of claim 2, where M is W.

5. The compound of any one of claims 1 to 4, wherein n is 0.

6. The compound of any one of claims 1 to 5, wherein X is an oxygen atom.

7. The compound of any one of claims 1 to 5, wherein X is ═

N—

R⁵.

8. The compound of claim 7, wherein R⁵ is C_3-12 cycloalkyl, C_6-20 aryl, or C_2-20 heteroaryl, each of which is optionally substituted one or more times with substituents selected independently from R³¹, wherein any two adjacent R³¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

9. The compound of claim 8, wherein R⁵ is C_3-12 cycloalkyl, phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, or 2-pyrazinyl, each of which is optionally substituted one or more times with substituents selected independently from R³¹, wherein any two adjacent R³¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

10. The compound of claim 9, wherein R⁵ is C_3-12 cycloalkyl, phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, or 2-pyrazinyl, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, and —

O—

Si(C_1-6 alkyl)₃.

11. The compound of claim 10, wherein R⁵ is C_3-12 cycloalkyl or phenyl, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, and —

O—

Si(C_1-6 alkyl)₃.

12. The compound of claim 11, wherein R⁵ is C_3-12 cycloalkyl or phenyl, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom and C_1-6 alkyl.

13. The compound of claim 12, wherein R⁵ is adamantyl or phenyl, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom and C_1-6 alkyl.

14. The compound of claim 13, wherein R⁵ is phenyl, which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom and C_1-6 alkyl.

15. The compound of any one of claims 1 to 14, wherein R¹ is hydrogen, C_1-6 alkyl, or —

O—

(C_1-6 alkyl).

16. The compound of claim 15, wherein R¹ is hydrogen.

17. The compound of any one of claims 1 to 16, wherein R² is phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, or 2-pyrazinyl, each of which is optionally substituted one or more times by substituents selected independently from R⁶, wherein any two adjacent R⁶ optionally combine to form a ring, which is optionally substituted one or more times by substituents selected independently from R^x.

18. The compound of claim 17, wherein R² is phenyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, or 2-pyrazinyl, each of which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SH, —

S(C_1-6 alkyl), —

C(O)—

(C_1-6 alkyl), —

CHO, —

O—

C(O)—

(C_1-6 alkyl), —

C(O)—

O—

(C_1-6 alkyl), —

CO₂H, —

O—

C(O)—

O—

(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

O—

SO₂(C_1-6 alkyl), —

SO₂—

O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

NH—

CO₂H, —

N(C_1-6 alkyl)-CO₂H, —

NH—

C(O)—

O(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

O—

C(O)NH₂, —

O—

C(O)NH(C_1-6 alkyl), —

O—

C(O)N(C_1-6 alkyl)₂, —

NH—

C(O)NH₂, —

NH—

C(O)NH(C_1-6 alkyl), —

NH—

C(O)N(C_1-6 alkyl)₂, —

N(C_1-6 alkyl)-C(O)NH₂, —

N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, —

O—

Si(C_1-6 alkyl)₃, —

(C_1-6 alkylene)-C_3-10 cycloalkyl, —

(C_1-6 alkylene)-phenyl, —

(C_1-6 alkylene)-CN, —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

(C_1-6 alkylene)-SH, —

(C_1-6 alkylene)-S(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CHO, —

(C_1-6 alkylene)-O—

C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CO₂H, —

(C_1-6 alkylene)-O—

C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-C(O)NH₂, —

(C_1-6 alkylene)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

CO₂H, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-CO₂H, —

(C_1-6 alkylene)-NH—

C(O)—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)NH₂, —

(C_1-6 alkylene)-O—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

C(O)NH₂, —

(C_1-6 alkylene)-NH—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-NH—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-Si(C_1-6 alkyl)₃, and —

(C_1-6 alkylene)-O—

Si(C_1-6 alkyl)₃.

19. The compound of claim 17, wherein R² is phenyl, which is optionally substituted one or more times by substituents selected independently from R⁶, wherein any two adjacent R⁶ optionally combine to form a ring.

20. The compound of claim 17, wherein R² is phenyl, which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SH, —

S(C_1-6 alkyl), —

C(O)—

(C_1-6 alkyl), —

CHO, —

O—

C(O)—

(C_1-6 alkyl), —

C(O)—

O—

(C_1-6 alkyl), —

CO₂H, —

O—

C(O)—

O—

(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

O—

SO₂(C_1-6 alkyl), —

SO₂—

O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

NH—

CO₂H, —

N(C_1-6 alkyl)-CO₂H, —

NH—

C(O)—

O(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

O—

C(O)NH₂, —

O—

C(O)NH(C_1-6 alkyl), —

O—

C(O)N(C_1-6 alkyl)₂, —

NH—

C(O)NH₂, —

NH—

C(O)NH(C_1-6 alkyl), —

NH—

C(O)N(C_1-6 alkyl)₂, —

N(C_1-6 alkyl)-C(O)NH₂, —

N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, —

O—

Si(C_1-6 alkyl)₃, —

(C_1-6 alkylene)-C_3-10 cycloalkyl, —

(C_1-6 alkylene)-phenyl, —

(C_1-6 alkylene)-CN, —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

(C_1-6 alkylene)-SH, —

(C_1-6 alkylene)-S(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CHO, —

(C_1-6 alkylene)-O—

C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CO₂H, —

(C_1-6 alkylene)-O—

C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-C(O)NH₂, —

(C_1-6 alkylene)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

CO₂H, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-CO₂H, —

(C_1-6 alkylene)-NH—

C(O)—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)NH₂, —

(C_1-6 alkylene)-O—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

C(O)NH₂, —

(C_1-6 alkylene)-NH—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-NH—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-Si(C_1-6 alkyl)₃, and —

(C_1-6 alkylene)-O—

Si(C_1-6 alkyl)₃.

21. The compound of claim 20, wherein R² is phenyl, which is optionally substituted one or more times with substituents selected independently from a halogen atom, —

OH, —

O(C_1-6 alkyl), —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), and —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂.

22. The compound of claim 20, wherein R² is 2-(C_1-6 alkyloxy)phenyl, where the phenyl ring is further optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SH, —

S(C_1-6 alkyl), —

C(O)—

(C_1-6 alkyl), —

CHO, —

O—

C(O)—

(C_1-6 alkyl), —

C(O)—

O—

(C_1-6 alkyl), —

CO₂H, —

O—

C(O)—

O—

(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

O—

SO₂(C_1-6 alkyl), —

SO₂—

O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

NH—

CO₂H, —

N(C_1-6 alkyl)-CO₂H, —

NH—

C(O)—

O(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

O—

C(O)NH₂, —

O—

C(O)NH(C_1-6 alkyl), —

O—

C(O)N(C_1-6 alkyl)₂, —

NH—

C(O)NH₂, —

NH—

C(O)NH(C_1-6 alkyl), —

NH—

C(O)N(C_1-6 alkyl)₂, —

N(C_1-6 alkyl)-C(O)NH₂, —

N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, —

O—

Si(C_1-6 alkyl)₃, —

(C_1-6 alkylene)-C_3-10 cycloalkyl, —

(C_1-6 alkylene)-phenyl, —

(C_1-6 alkylene)-CN, —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

(C_1-6 alkylene)-SH, —

(C_1-6 alkylene)-S(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CHO, —

(C_1-6 alkylene)-O—

C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CO₂H, —

(C_1-6 alkylene)-O—

C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-C(O)NH₂, —

(C_1-6 alkylene)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

CO₂H, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-CO₂H, —

(C_1-6 alkylene)-NH—

C(O)—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)NH₂, —

(C_1-6 alkylene)-O—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

C(O)NH₂, —

(C_1-6 alkylene)-NH—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-NH—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-Si(C_1-6 alkyl)₃, and —

(C_1-6 alkylene)-O—

Si(C_1-6 alkyl)₃.

23. The compound of claim 22, wherein R² is 2-(C_1-6 alkyloxy)phenyl, which is optionally substituted one or more times with substituents selected independently from a halogen atom, —

OH, —

O(C_1-6 alkyl), —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), and —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂.

24. The compound of claim 17, wherein R² is 2-pyridyl, which is optionally substituted one or more times by substituents selected independently from R⁶, wherein any two adjacent R⁶ optionally combine to form a ring.

25. The compound of claim 17, wherein R² is 2-pyridyl, which is optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

OH, —

O(C_1-6 alkyl), —

SH, —

S(C_1-6 alkyl), —

C(O)—

(C_1-6 alkyl), —

CHO, —

O—

C(O)—

(C_1-6 alkyl), —

C(O)—

O—

(C_1-6 alkyl), —

CO₂H, —

O—

C(O)—

O—

(C_1-6 alkyl), —

SO₂(C_1-6 alkyl), —

O—

SO₂(C_1-6 alkyl), —

SO₂—

O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

C(O)NH₂, —

C(O)NH(C_1-6 alkyl), —

C(O)N(C_1-6 alkyl)₂, —

NH—

CO₂H, —

N(C_1-6 alkyl)-CO₂H, —

NH—

C(O)—

O(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

O—

C(O)NH₂, —

O—

C(O)NH(C_1-6 alkyl), —

O—

C(O)N(C_1-6 alkyl)₂, —

NH—

C(O)NH₂, —

NH—

C(O)NH(C_1-6 alkyl), —

NH—

C(O)N(C_1-6 alkyl)₂, —

N(C_1-6 alkyl)-C(O)NH₂, —

N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

Si(C_1-6 alkyl)₃, —

O—

Si(C_1-6 alkyl)₃, —

(C_1-6 alkylene)-C_3-10 cycloalkyl, —

(C_1-6 alkylene)-phenyl, —

(C_1-6 alkylene)-CN, —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

(C_1-6 alkylene)-SH, —

(C_1-6 alkylene)-S(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CHO, —

(C_1-6 alkylene)-O—

C(O)—

(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-CO₂H, —

(C_1-6 alkylene)-O—

C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

SO₂(C_1-6 alkyl), —

(C_1-6 alkylene)-SO₂—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-C(O)NH₂, —

(C_1-6 alkylene)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

CO₂H, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-CO₂H, —

(C_1-6 alkylene)-NH—

C(O)—

O(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)—

O—

(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)NH₂, —

(C_1-6 alkylene)-O—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-O—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH—

C(O)NH₂, —

(C_1-6 alkylene)-NH—

C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-NH—

C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH₂, —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)NH(C_1-6 alkyl), —

(C_1-6 alkylene)-N(C_1-6 alkyl)-C(O)N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-Si(C_1-6 alkyl)₃, and —

(C_1-6 alkylene)-O—

Si(C_1-6 alkyl)₃.

26. The compound of claim 25, wherein R² is 2-pyridyl, which is optionally substituted one or more times with substituents selected independently from a halogen atom, —

OH, —

O(C_1-6 alkyl), —

(C_1-6 alkylene)-OH, —

(C_1-6 alkylene)-O(C_1-6 alkyl), —

NH₂, —

NH(C_1-6 alkyl), —

N(C_1-6 alkyl)₂, —

(C_1-6 alkylene)-NH₂, —

(C_1-6 alkylene)-NH(C_1-6 alkyl), and —

(C_1-6 alkylene)-N(C_1-6 alkyl)₂.

27. The compound of any one of claims 1 to 16, wherein R² is -G¹⁰-R³³.

28. The compound of claim 27, wherein G¹⁰ is —

O—

or —

S—

.

29. The compound of claim 28, wherein G¹⁰ is —

O—

.

30. The compound of any one of claims 27 to 29, wherein R³³ is C_2-20 heterocyclyl, which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

31. The compound of claim 30, wherein R³³ is C_2-20 heterocyclyl, which has a heteroatom at the 2-position relative to the attachment point of the heterocyclyl group to G¹⁰, wherein said heteroatom is an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom, and which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

32. The compound of claim 31, wherein R³³ is 2-tetrahydropyranyl, which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

33. The compound of any one of claims 27 to 29, wherein R³³ is C_2-20 heteroaryl, which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

34. The compound of claim 33, wherein R³³ is C_2-20 heteroaryl, which has a heteroatom at the 2-position relative to the attachment point of the heteroaryl group to G¹⁰, wherein said heteroatom is an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom, and which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

35. The compound of claim 34, wherein R³³ is 2-pyridyl, which is optionally substituted one or more times by substituents selected independently from R⁴¹, wherein any two adjacent R⁴¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

36. The compound of any one of claims 27 to 29, wherein R³³ is C_2-20 heteroalkyl, which is optionally substituted one or more times by substituents selected independently from R⁴².

37. The compound of claim 36, wherein In some such embodiments, R³³ is C_2-20 heteroalkyl, which has a heteroatom at the 2-position relative to the attachment point of the heteroalkyl group to G¹⁰, wherein said heteroatom is an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom, which is optionally substituted one or more times by substituents selected independently from R⁴².

38. The compound of claim 37, wherein R³³ is —

CH₂—

O—

(C_1-10 alkyl), —

CH(C_1-6 alkyl)-O—

(C_1-10 alkyl), or —

C(C_1-6 alkyl)₂-O—

(C_1-6 alkyl).

39. The compound of any one of claims 1 to 38, wherein R³ is —

OR⁷ or —

SR⁷.

40. The compound of claim 39, wherein R³ is —

OR⁷.

41. The compound of claim 40, wherein R⁷ is -G⁷-R¹⁷.

42. The compound of claim 41, wherein -G⁷-R¹⁷ is C_1-12 alkyl, which is optionally substituted one or more times with substituents selected independently from R³².

43. The compound of claim 42, wherein -G⁷-R¹⁷ is C_1-12 alkyl, which is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom and phenyl, wherein the phenyl group is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, —

O—

(C_1-6 alkyl), C_1-6 haloalkyl, —

O—

(C_1-6 haloalkyl), —

Si—

(C_1-6 alkyl)₃, and —

O—

Si(C_1-6 alkyl)₃.

44. The compound of claim 43, wherein -G⁷-R¹⁷ is C_1-12 alkyl, which is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom and phenyl.

45. The compound of claim 41, wherein -G⁷-R¹⁷ is tert-butyl, —

C(CH₃)₂(CF₃), —

C(CF₃)₃, or —

C(CF₃)₂-(phenyl).

46. The compound of claim 40, wherein R⁷ is C_6-20 aryl or C_2-20 heteroaryl, each of which is optionally substituted one or more times with substituents selected independently from R³¹, wherein any two adjacent R³¹ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

47. The compound of claim 46, wherein R⁷ is phenyl, 1-naphthyl, or 2-naphthyl, each of which is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_2-6 alkenyl, C_3-10 cycloalkyl, phenyl, 1-naphthyl, 2-naphthyl, —

CN, —

O(C_1-6 alkyl), —

Si(C_1-6 alkyl)₃, and —

O—

Si(C_1-6 alkyl)₃, or any two adjacent substituents can optionally combine to form a —

(CH₂)₄—

ring or a —

(CH)₄—

ring, wherein the cycloalkyl, phenyl, and naphthyl substituents are optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, C_3-10 cycloalkyl, phenyl, —

CN, —

O(C_1-6 alkyl), —

Si(C_1-6 alkyl)₃, and —

O—

Si(C_1-6 alkyl)₃, or any two adjacent substituents can optionally combine to form a —

(CH₂)₄—

ring or a —

(CH)₄—

ring.

48. The compound of claim 47, wherein R⁷ is phenyl or 1-naphthyl, each of which is optionally substituted one or more times with substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, phenyl, 1-naphthyl, —

O(C_1-6 alkyl), and —

O—

Si(C_1-6 alkyl)₃, or any two adjacent alkyl substituents can optionally combine to form a —

(CH₂)₄—

ring, wherein the phenyl and naphthyl substituents are optionally substituted one or more times by substituents selected independently from the group consisting of a halogen atom, C_1-6 alkyl, phenyl, —

O(C_1-6 alkyl), and —

O—

Si(C_1-6 alkyl)₃, or any two adjacent alkyl substituents can optionally combine to form a —

(CH₂)₄—

ring.

49. The compound of any one of claims 1 to 48, wherein R⁴ is —

O—

SiR²¹R²²R²³.

51. The compound of any one of claims 1 to 48, wherein R⁴ is —

O—

CR²¹R²²R²³.

52. The compound of claim 51, wherein R⁴ is —

O—

C—

(CF₃)₂(CH₃).

53. The compound of any one of claims 1 to 48, wherein R⁴ is pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, 1H-1,2,3-triazol-1-yl, 2H-1,2,3-triazol-2-yl, 1H-1,2,4-triazol-1-yl, or 4H-1,2,4-triazol-4-yl, each of which is optionally substituted one or more times with substituents selected independently from R⁸, wherein any two adjacent R⁸ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

54. The compound of claim 53, wherein R⁴ is pyrrol-1-yl or imidazol-1-yl, each of which is optionally substituted one or more times with substituents selected independently from R⁸, wherein any two adjacent R⁸ optionally combine to form a ring, which is optionally substituted one or more times with substituents selected independently from R^x.

55. The compound of claim 54, wherein R⁴ is pyrrol-1-yl or imidazol-1-yl, each of which is optionally substituted one or more times with substituents selected independently from the group consisting of a C_1-6 alkyl, C_2-6 alkenyl, and phenyl, or any two adjacent substituents can optionally combine to form a —

(CH)₄—

ring.

56. The compound of any one of claims 1 to 55, wherein the compound is any one of Compounds 1 to 40 in Table 2.

66. A method for carrying out a metathesis reaction, the method comprising:

providing a first compound having one or more carbon-carbon double bonds; and

reacting the first compound via a metathesis reaction in the presence of a compound of any one of claims 1 to 65.

67. The method of claim 66, wherein the first compound has two or more carbon-carbon double bonds.

68. The method of claim 66 or 67, wherein the metathesis reaction is a ring-closing metathesis reaction between two of the two or more carbon-carbon double bonds of the first compound.

69. The method of any one of claims 66 to 68, wherein a catalytically effective amount of the metathesis catalyst is present.

70. A method of carrying out a metathesis reaction, the method comprising:

providing a first compound having one or more carbon-carbon double bond and a second compound having one or more carbon-carbon double bonds; and

reacting the first compound and the second compound via a metathesis reaction in the presence of a compound of any one of claims 1 to 65.

71. The method of claim 70, wherein the first compound and the second compound are the same compound.

72. The method of claim 70, wherein the first compound and the second compound are not the same.

73. The method of claim 72, wherein the first compound is an internal olefin.

74. The method of claim 72 or 73, wherein the second compound is a short-chain alkene.

75. The method of claim 74, wherein the short-chain alkene is ethylene.

76. The method of any one of claims 70 to 75, wherein a catalytically effective amount of the metathesis catalyst is present.

50. The compound of claim 50, wherein R⁴ is —

O—

Si—

(C_1-6 alkyl)₃ or —

O—

Si-(phenyl)₃.

57. A compound of Formula (II)

58. The compound of claim 57, wherein R¹⁰¹ is phenyl, 2,6-dichlorophenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, 2-trifluoromethylphenyl, pentafluorophenyl, tert-butyl, or 1-adamantyl.

59. The compound of claim 57 or 58, wherein R¹⁰² is pyrrol-1-yl, 2,5-dimethylpyrrol-1-yl, 2,5-diphenylpyrrol-1-yl, 2,5-dimethylimidazol-1-yl, or indol-1-yl.

60. The compound of any one of claims 57 to 59, wherein R¹⁰³ is 2,6-diphenylphenyl, 4-bromo-2,3,5,6-tetraphenylphenyl, tert-butyl, —

C(CH₃)₂CF₃, C(CF₃)₃, or —

C(CF₃)₂(phenyl).

61. The compound of any one of claims 57 to 59, wherein R¹⁰³ is:

62. The compound of any one of claims 57 to 61, wherein R¹⁰⁴ is a hydrogen atom.

63. The compound of any one of claims 57 to 62, wherein R¹⁰⁵ is a hydrogen atom, methyloxy, ethyloxy, methyloxymethyloxy, isopropyloxy, or dimethylamino.

64. The compound of any one of claims 57 to 63, wherein R¹⁰⁶ and R¹⁰⁷ are independently a hydrogen atom, methyl, a halogen atom, or methyloxy.

65. The compound of any one of claims 57 to 64, wherein the compound is any one of Compounds 1 to 34 in Table 2.