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Synfacts 2009(11): 1264-1264  
DOI: 10.1055/s-0029-1218050
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Au/Mo-Catalyzed Synthesis of α-Halo-α,β-unsaturated Carbonyls

Contributor(s): Paul Knochel, Andreas J. Wagner
L. Ye, L. Zhang*
University of Nevada, Reno, USA
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

A direct, efficient synthesis of α-iodo/bromo-α,β-unsaturated aldehydes and ­ketones from propargylic alcohols is reported. Two metal complexes, Ph3PAuNTf2 and MoO2(acac)2, collaboratively catalyze this transformation, and undesired enone/enal formation is effectively inhibited by using Ph3PO as additive. Low catalyst loadings are required, the conditions are mild and the diastereoselectivity is good to ­excellent.