Addition of bifunctional organoboron reagents to strained alkenes. Carbon-carbon bond formation with Rh (I) catalysis in aqueous media

M Lautens, J Mancuso

Index: Lautens, Mark; Mancuso, John Journal of Organic Chemistry, 2004 , vol. 69, # 10 p. 3478 - 3487

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Citation Number: 64

Abstract

Arylboronate esters bearing a pendant Michael-type acceptor olefin undergo transmetalation with a rhodium-based catalytic complex to generate a functionalized organorhodium intermediate that can cyclize onto strained olefins in good to excellent yields. The catalytic system involves the use of an electron-rich, sterically bulky ligand to stabilize the organorhodium intermediate and reduce the incidence of protodeboronation ...