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Letter

Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents: Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄

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Jong Uk Rhee and Michael J. Krische*

Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712

Org. Lett., 2005, 7 (12), pp 2493–2495

DOI: 10.1021/ol050838x

Publication Date (Web): May 11, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mkrische@mail.utexas.edu

Abstract

The first use of cationic silver (AgSbF₄) as a catalyst for intra- and intermolecular alkyne−carbonyl coupling to form conjugated enones is described, and a comparison to corresponding Brønsted acid (HBF₄) and Lewis acid (BF₃) catalyst systems is made. Notably, intermolecular coupling proceeds stereoselectively to afford the corresponding trisubstituted enones as single geometrical isomers. This transformation represents a completely atom economical alternative to the use of stabilized Wittig reagents in carbonyl olefination and may be viewed as a formal alkyne−carbonyl metathesis.

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Published In Issue June 09, 2005
Received April 16, 2005

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Letter

Alkynes as Synthetic Equivalents to Stabilized Wittig Reagents: Intra- and Intermolecular Carbonyl Olefinations Catalyzed by Ag(I), BF₃, and HBF₄