Organic letters

α-Palladation of imines as entry to dehydrogenative Heck reaction: aerobic oxidative cyclization of N-allylimines to pyrroles

Z Chen, B Lu, Z Ding, K Gao, N Yoshikai

Index: Chen, Zhiyuan; Lu, Beili; Ding, Zhenhua; Gao, Ke; Yoshikai, Naohiko Organic Letters, 2013 , vol. 15, # 8 p. 1966 - 1969

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Citation Number: 39

Abstract

We report here a palladium (II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization.