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Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions.

ABSTRACT: A Cu-catalyzed method for efficient boron-copper addition processes involving acyclic and cyclic disubstituted aryl olefins are reported. Reactions are promoted with 0.5-5 mol % of a readily available N-heterocyclic carbene (NHC) complex; the presence of MeOH promotes in situ protonation of the C-Cu bond and leads to efficient catalyst turnover, constituting a net Cu-catalyzed hydroboration process. Reactions proceed in >98:<2 site selectivity and furnish secondary organoborane isomers that complement those obtained through reactions of boron-hydride reagents or by Rh- or Ir-catalyzed hydroborations (benzylic secondary C-B bonds). Initial observations regarding processes catalyzed by chiral NHC complexes, delivering products in up to 99:1 enantiomeric ratio, are disclosed.

SUBMITTER: Lee Y

PROVIDER: S-EPMC2662741 | biostudies-literature | 2009 Mar

REPOSITORIES: biostudies-literature

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Efficient boron-copper additions to aryl-substituted alkenes promoted by NHC-based catalysts. enantioselective Cu-catalyzed hydroboration reactions.

Lee Yunmi Y Hoveyda Amir H AH

Journal of the American Chemical Society 20090301 9

A Cu-catalyzed method for efficient boron-copper addition processes involving acyclic and cyclic disubstituted aryl olefins are reported. Reactions are promoted with 0.5-5 mol % of a readily available N-heterocyclic carbene (NHC) complex; the presence of MeOH promotes in situ protonation of the C-Cu bond and leads to efficient catalyst turnover, constituting a net Cu-catalyzed hydroboration process. Reactions proceed in >98:<2 site selectivity and furnish secondary organoborane isomers that comp ...[more]

PMID: 19256564

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