An Opportunity for Mg-Catalyzed Grignard-Type Reactions: Direct Coupling of Benzylic Halides with Pinacolborane with 10 mol % of Magnesium
Christine Pintaric, Sandra Olivero, Yves Gimbert, Pierre Y. Chavant and Elisabet Duņach*
*Laboratoire de Chimie des Molcules Bioactives et des Armes,
Universit de Nice-Sophia Antipolis, CNRS-UMR 6001, Institut de Chimie de Nice,
28, avenue de Valrose F-06108 Nice, France, Email: dunach
unice.fr
C. Pintaric, S. Olivero, Y. Gimbert, P. Y. Chavant, E. Duņach, J. Am. Chem. Soc., 2010, 132, 11825-11827.
DOI: 10.1021/ja1052973
Abstract
A catalytic amount of Mg as the only metal enables a reductive coupling between benzyl halides and pinacolborane. HBpin acts both as an electrophile and as a reducing agent to regenerate an organomagnesium species in situ. An hydride oxidation mechanism is proposed on the basis of DFT calculations.
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ID: J48-Y2010-2390
