Tetrahedron

A simple iodination protocol via in situ generated ICl using NaI/FeCl 3

AK Mohanakrishnan, C Prakash, N Ramesh

Index: Mohanakrishnan, Arasambattu K.; Prakash, Chandran; Ramesh, Neelamegam Tetrahedron, 2006 , vol. 62, # 14 p. 3242 - 3247

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Citation Number: 24

Abstract

In an ongoing project we required a wide variety of α-bromo/iodo ketones for our work on the synthesis of carbocyclic natural products involving a tandem cyclization of a α-carbonyl radical. The required silyl-enol ethers were smoothly prepared via a CuI promoted 1,4-addition of various Grignards to enones. Initially the iodination/bromination of silyl-enol ether 1a was tried using NIS/NBS without any success. The existing procedure for iodination using NaI/m- ...