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US 2010/0160642 A1Published application
Catalyst Complex With Carbene Ligand
AssigneeUniversity of New Orleans Research and Technology Foundation, Inc.
InventorsSteven P. Nolan, Jinkun Huang
Life of this patent
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Abstract
Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbine ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.
Claims6
A catalytic complex of the formula:
- wherein either or both of C1 and C2 are optionally absent;
- where
- M is Os or Ru;
- R and R1 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C2-C20 alkoxycarbonyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, each R and R1 optionally being substituted with C1-C5 alkyl, halogen, C1-C10 alkoxy, or with a phenyl group substituted with halogen, C1-C5 alkyl or C1-C5 alkoxy, or with a functional group;
- X and X1 are independently selected from the group consisting of anionic ligands;
- and
- L and L1 are nucleophilic carbenes, each nucleophilic carbene comprising a carbene carbon further bonded to two heteroatoms independently selected from the group consisting of oxygen and sulfur.
4 more elements
A catalytic complex of the formula:
- where
- M is Os or Ru;
- R and R1 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C2-C20 alkoxycarbonyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C1-C20 alkylthio, C1-C20 alkylsulfonyl, and C1-C20 alkylsulfinyl, each R and R1 optionally being substituted with C1-C5 alkyl, halogen, C1-C10 alkoxy, or with a phenyl group substituted with halogen, C1-C5 alkyl or C1-C5 alkoxy, or with a functional group;
- X and X1 are independently selected from the group consisting of anionic ligands;
- and
- L and L1 are nucleophilic carbenes of the formula
- wherein
- Y and Y1 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C2-C20 alkoxycarbonyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, and aryloxy, each Y and Y1 optionally being substituted with C1-C5 alkyl, halogen, C1-C6 alkoxy, or with a phenyl group substituted with halogen, C1-C5 alkyl or C1-C5 alkoxy;
- and
- Z and Z1 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C2-C20 alkoxycarbonyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, and aryloxy, each Z and Z1 optionally being substituted with C1-C5 alkyl, halogen, C1-C6 alkoxy, or with a phenyl group substituted with halogen, C1-C5 alkyl or C1-C5 alkoxy.
7 more elements
A method of making a nucleophilic carbene, said method comprising:
- a) contacting either (i) a substituted or unsubstituted phenol or an alcohol, or (ii) a substituted or unsubstituted benzenethiol or a thiol, with an approximately one-half equimolar amount of paraformaldehyde under an inert atmosphere to make a first reaction mixture;
- b) heating said first reaction mixture until said paraformaldehyde dissolves;
- c) adding an approximately one-half equimolar amount of a mineral acid to make a second reaction mixture;
- and
- c) heating said second reaction mixture for a time and under conditions sufficient to make a nucleophilic carbene.
2 more elements
Dependencies are inferred from the claim text.