A Unique Catalyst Effects the Rapid Room-Temperature Cross-Coupling of Organozinc Reagents with Carboxylic Acid Fluorides, Chlorides, Anhydrides, and Thioesters

Yongda Zhang and Tomislav Rovis*
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80526
J. Am. Chem. Soc., 2004, 126 (49), pp 15964–15965
DOI: 10.1021/ja044113k
Publication Date (Web): November 18, 2004
Copyright © 2004 American Chemical Society
*

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

, rovis@lamar.colostate.edu

Abstract

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We have identified a catalyst capable of effecting the rapid, room-temperature cross-coupling between acid fluorides and diorganozinc reagents. The use of acid fluorides as electrophilic partners allows this reaction to tolerate epimerizable functionality as well as β leaving groups. The same catalyst is also capable of cross-coupling acid chlorides, acyl cyanides, anhydrides, thioesters, and pyridyl esters. Noteworthy is the ability of the reaction to successfully transfer both groups from the organometalic fragment.

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History

  • Published In Issue December 15, 2004
  • Received September 27, 2004

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