Copper-Catalyzed C−P Bond Construction via Direct Coupling of Secondary Phosphines and Phosphites with Aryl and Vinyl Halides

Dmitri Gelman, Lei Jiang, and Stephen L. Buchwald*
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts, 02139
Org. Lett., 2003, 5 (13), pp 2315–2318
DOI: 10.1021/ol0346640
Publication Date (Web): May 23, 2003
Copyright © 2003 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.

, sbuchwal@mit.edu

Abstract

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A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N‘-dimethylethylenediamine as a ligand, and Cs2CO3 as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields.

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History

  • Published In Issue June 26, 2003
  • Received April 18, 2003

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