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Practical Synthesis of Linear α-Iodo/Bromo-α,β-unsaturated Aldehydes/Ketones from Propargylic Alcohols via Au/Mo Bimetallic Catalysis

Longwu Ye and Liming Zhang*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, CA 93106-9510, Email: zhangchem.ucsb.edu

L. Ye, L. Zhang, Org. Lett., 2009, 11, 3646-3649.

DOI: 10.1021/ol901346k (free Supporting Information)


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Abstract

An efficient synthesis of α-iodo/bromo-α,β-unsaturated aldehydes/ketones directly from propargylic alcohols is catalyzed collaboratively by Ph3PAuNTf2 and MoO2(acac)2, and Ph3PO as an additive helps suppress undesired enone/enal formation. Notable features of this method include low catalyst loadings, mild reaction conditions, and mostly good diastereoselectivity.

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Gold-Catalyzed Efficient Preparation of Linear α-Iodoenones from Propargylic Acetates

M. Yu, G. Zhang, L. Zhang, Org. Lett., 2007, 9, 2087-2090.


Key Words

Iodination, Bromination, NIS, NBS, Enones, Alkenyl Halides


ID: J54-Y2009-2500