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Communication

Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond

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David S. Laitar, Emily Y. Tsui, and Joseph P. Sadighi*

Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2006, 128 (34), pp 11036–11037

DOI: 10.1021/ja064019z

Publication Date (Web): August 4, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jsadighi@mit.edu

Abstract

Mesitaldehyde reacts cleanly with (IPr)CuB(pin) [IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); pin = 2,3-dimethyl-2,3-butanediolate] to afford the product complex 1, the first well-defined product of carbonyl group insertion into a metal−boron bond. Analysis of 1 by NMR spectroscopy and single-crystal X-ray diffraction indicates the formation of a copper−carbon and a boron−oxygen bond. A copper(I) precatalyst supported by the less sterically demanding ligand ICy (1,3-dicyclohexylimidazol-2-ylidene) achieves the efficient 1,2-diboration of aryl-, heteroaryl-, and alkyl-substituted aldehydes at room temperature.

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Published In Issue August 30, 2006
Received June 7, 2006

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Communication

Catalytic Diboration of Aldehydes via Insertion into the Copper−Boron Bond

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Efficient Boron−Copper Additions to Aryl-Substituted Alkenes Promoted by NHC−Based Catalysts. Enantioselective Cu-Catalyzed Hydroboration Reactions

Nickel-Catalyzed β-Boration of α,β-Unsaturated Esters and Amides with Bis(pinacolato)diboron

Asymmetric Copper-Catalyzed Synthesis of α-Amino Boronate Esters from N-tert-Butanesulfinyl Aldimines

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