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Design and synthesis of C2-symmetric N-heterocyclic carbene precursors and metal carbenoids.

ABSTRACT: Chiral, C(2)-symmetric imidazolium and imidazolinium ions, as well as the corresponding copper- or silver-bound carbenoids, have been prepared. Structural study of these compounds by X-ray crystallography reveals a chiral pocket that surrounds the putative carbene site or the metal-carbene bond, at carbon 2, in three of the four ligands prepared. Preliminary investigation into the application of these complexes has shown one of them to be highly enantioselective in the hydrosilylation of acetophenone.

SUBMITTER: Albright A

PROVIDER: S-EPMC3172702 | biostudies-literature | 2011 Sep

REPOSITORIES: biostudies-literature

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Design and synthesis of C2-symmetric N-heterocyclic carbene precursors and metal carbenoids.

Albright Abigail A Eddings Daniel D Black Regina R Welch Christopher J CJ Gerasimchuk Nikolay N NN Gawley Robert E RE

The Journal of organic chemistry 20110825 18

Chiral, C(2)-symmetric imidazolium and imidazolinium ions, as well as the corresponding copper- or silver-bound carbenoids, have been prepared. Structural study of these compounds by X-ray crystallography reveals a chiral pocket that surrounds the putative carbene site or the metal-carbene bond, at carbon 2, in three of the four ligands prepared. Preliminary investigation into the application of these complexes has shown one of them to be highly enantioselective in the hydrosilylation of acetoph ...[more]

PMID: 21823580

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