Regiospecific functionalization of methyl CH bonds of alkyl groups in reagents with heteroatom functionality

JD Lawrence, M Takahashi, C Bae…

Index: Lawrence, Joshua D.; Takahashi, Makoto; Bae, Chulsung; Hartwig, John F. Journal of the American Chemical Society, 2004 , vol. 126, # 47 p. 15334 - 15335

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Citation Number: 95

Abstract

We report the regiospecific, rhodium-catalyzed borylation of saturated terminal CH bonds in molecules with existing functionality. Moderate to good yields were obtained with the organic substrate in excess and as limiting reagent. The borylations of trialkylamines, protected alcohols, protected ketones, and fluoroalkanes occurred regiospecifically at the methyl group that is least sterically hindered. Reactions were also conducted that probed ...