Abstract: The present invention relates to novel hexacoordinated metathesis catalysts and to methods for making and using the same. The inventive catalysts are of the formula
wherein:
M is ruthenium or osmium;
X and X1 are the same or different and are each independently an anionic ligand;
L, L1′ and L2 are the same or different and are each independently a neutral electron donor ligand; and,
R and R1 are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl and silyl.
Type:
Grant
Filed:
June 14, 2002
Date of Patent:
November 16, 2004
Assignees:
Cymetech, LLP, California Institute of Technology
Inventors:
Robert H. Grubbs, Melanie S. Sanford, Jason L. Moore, Jennifer A. Love, Tina M. Trnka
Abstract: The present invention relates to novel hexacoordinated metathesis catalysts and to methods for making and using the same. The inventive catalysts are of the formula
wherein:
M is ruthenium or osmium;
X and X1 are the same or different and are each independently an anionic ligand;
L, L1′ and L2 are the same or different and are each independently a neutral electron donor ligand, wherein at least one L, L1′ and L2 is an N-heterocyclic carbene ligand; and,
R and R1 are each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.
Type:
Grant
Filed:
December 14, 2001
Date of Patent:
July 6, 2004
Assignees:
California Institute of Technology, Cymetech, LLP
Inventors:
Robert H. Grubbs, Jennifer A. Love, Melanie S. Sanford, Tina M. Trnka, Jason L. Moore
Abstract: The invention provides a process for the in-situ generation of a metathesis active catalyst of the formula:
comprising contacting an NHC carbene with a dimer of the formula [(arene)MX1X]2 and an
alkyne of the formula RC≡CR1 or wherein
M is ruthenium or osmium;
X and X1 are the same or different and are each independently an anionic ligand;
NHC is any N-heterocyclic carbene ligand;
R, R1 and R2 are each independently hydrogen or a substituted or unsubstituted substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl; and
R3 is OH.
Preferably, the NHC is an s-IMES or IMES carbene ligand; the arene is preferably p-cymene and the alkyne is preferably acetylene.
Type:
Grant
Filed:
September 5, 2001
Date of Patent:
August 26, 2003
Assignees:
Cymetech, LLP, California Institute of Technology
Inventors:
Robert H. Grubbs, Janis Louie, John P. Morgan, Jason L. Moore