Organic letters

Biaryl Formation from 5-(2-Bromobenzyl)-Substituted Piperidin-2-ones via Palladacycles

G Satyanarayana, ME Maier

Index: Satyanarayana, Gedu; Maier, Martin E. Organic Letters, 2008 , vol. 10, # 12 p. 2361 - 2364

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Citation Number: 18

Abstract

The reaction of piperdin-2-ones with a 2-bromobenzyl substituent in the 5-position in the presence of a palladium catalyst leads to biaryl compounds. Their formation can be explained via initial C− H insertion of the aryl palladium species into the allylic C− H bond of the piperidinone. This eventually leads to a metallacycle containing Pd (II) that inserts another aryl bromide, promoting the formation of the biaryl bond.