Organic letters

CH Activation and palladium migration within biaryls under Heck reaction conditions

G Karig, MT Moon, N Thasana, T Gallagher

Index: Karig, Gunter; Thasana, Nopporn; Gallagher, Timothy Synlett, 2002 , # 5 p. 808 - 810

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Citation Number: 114

Abstract

Biaryl bromides such as 1 (R NO2, H, OMe) undergo the Heck reaction to give both the expected products 3 (“retention”) as well as “crossover” products 4 derived from a migration of Pd and net transfer of reactivity from one aryl ring to the other. Under the conditions used, crossover is increasingly favored when electron-deficient arenes are involved. Crossover products derived from transfer onto the pyridine ring have also been observed.