Organic letters

Carbon-Based Leaving Group in Substitution Reactions: Functionalization of sp3-Hybridized Quaternary and Tertiary Benzylic Carbon Centers

SJ Mahoney, T Lou, G Bondarenko, E Fillion

Index: Mahoney, Stuart J.; Lou, Tiantong; Bondarenko, Ganna; Fillion, Eric Organic Letters, 2012 , vol. 14, # 13 p. 3474 - 3477

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Citation Number: 14

Abstract

Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic Csp3–Csp3 bonds into Csp3–X bonds (X= C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically> 90%).

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