Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2??Amidodienes

RL Greenaway, CD Campbell…

Index: Greenaway, Rebecca L.; Campbell, Craig D.; Chapman, Helen A.; Anderson, Edward A. Advanced Synthesis and Catalysis, 2012 , vol. 354, # 17 p. 3187 - 3194

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Citation Number: 23

Abstract

Abstract Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium- catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/ termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5–8), and the nature of the alcohol and base. Reaction of the ...