Compounds and the use thereof in metathesis reactions
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: wherein: M is a Group 6 metal atom; X is an oxygen atom, ═N—R 5 , ═N—N(R 5 )(R 5′ ) or ═N—O—R 5 , R 5 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; R 1 is hydrogen or an organic substituent; R 2 is an aryl or heteroaryl group, each optionally substituted; R 3 is an anionic ligand; and R 4 is an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted.
1. A compound of Formula (II)
wherein:
M is a molybdenum atom or a tungsten atom;
R 101 is phenyl, alkyl, or cycloalkyl, each of which is optionally substituted;
R 102 is pyrrolyl or indolyl, each of which is optionally substituted;
R 103 is 2,6-diphenylphenyl or 4-bromo-2,3,5,6-tetraphenylphenyl, or
R 103 is:
wherein “iPr” refers to isopropyl, and “OTBDMS” refers to tert-butyldimethylsilyloxy;
R 104 is a hydrogen atom;
R 105 is —O—(C 1-6 alkyl) or —CH 2 —O—(C 1-6 alkyl); and
R 106 and R 107 are independently a hydrogen atom, C 1-6 alkyl, C 1-6 alkoxy, or a halogen atom.
2. The compound of claim 1 , wherein R 101 is phenyl, 2,6-dichlorophenyl, 2,6-dimethylphenyl, 2,6-diisopropylphenyl, 2-trifluoromethylphenyl, pentafluorophenyl, tert-butyl, or 1-adamantyl.
3. The compound of claim 1 , wherein R 102 is pyrrol-1-yl, 2,5-dimethylpyrrol-1-yl, 2,5-diphenylpyrrol-1-yl, or indol-1-yl.
4. The compound of claim 1 , wherein R 105 is methyloxy, ethyloxy, or isopropyloxy.
5. The compound of claim 1 , wherein R 106 and R 107 are independently a hydrogen atom, methyl, a halogen atom, or methyloxy.
6. 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 claim 1 .
7. The method of claim 6 , wherein the first compound has two or more carbon-carbon double bonds.
8. The method of claim 7 , 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.
9. A method of carrying out a metathesis reaction, the method comprising:
providing a first compound having one or more carbon-carbon double bonds 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 claim 1 .
10. The method of claim 9 , wherein the first compound and the second compound are the same compound.
11. The method of claim 9 , wherein the first compound and the second compound are not the same.
12. The method of claim 11 , wherein the first compound is an internal olefin.
13. The method of claim 12 , wherein the second compound is a short-chain alkene.
14. The method of claim 13 , wherein the short-chain alkene is ethylene.
15. The method of claim 10 wherein the first compound is an unsaturated ester.
16. The method of claim 14 , wherein the first compound is an unsaturated ester.
17. The compound of claim 1 , wherein M is a tungsten atom.
18. The compound of claim 1 , wherein:
M is a tungsten atom;
R 101 is 2,6-dichlorophenyl;
R 102 is 2,5-dimethylpyrrol-1-yl;
R 103 is:
wherein “OTBDMS” refers to tert-butyldimethylsilyloxy;
R 104 is hydrogen;
R 105 is methyloxy;
R 106 is hydrogen; and
R 107 is hydrogen.
19. The compound of claim 1 , comprising a neutral ligand.