Organic letters

Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates

J Tummatorn, GB Dudley

Index: Tummatorn, Jumreang; Dudley, Gregory B. Organic Letters, 2011 , vol. 13, # 6 p. 1572 - 1575

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Citation Number: 29

Abstract

Reductive cyclization of aryl and vinyl iodides tethered to vinylogous acyl triflates (VATs) induces a ring-expanding fragmentation to provide cyclic alkynyl ketones, including strained nine-membered cycloalkynes, in fair to excellent yield. The tandem cyclization/C− C bond- cleavage is initiated under carefully optimized conditions by halogen− metal exchange in the presence of carbonyl and vinyl triflate functionality. A modified protocol for alkylation of ...