Palladium-Catalyzed Negishi Cross-Coupling Reactions of Unactivated Alkyl Iodides, Bromides, Chlorides, and Tosylates

Jianrong Zhou and Gregory C. Fu*
Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139
J. Am. Chem. Soc., 2003, 125 (41), pp 12527–12530
DOI: 10.1021/ja0363258
Publication Date (Web): September 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.

, gcf@mit.edu

Abstract

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A single method (2% Pd2(dba)3/8% PCyp3/NMI in THF/NMP at 80 °C; Cyp = cyclopentyl) achieves the cross-coupling of a range of β-hydrogen-containing primary alkyl iodides, bromides, chlorides, and tosylates with an array of alkyl-, alkenyl-, and arylzinc halides. The process is compatible with a variety of functional groups, including esters, amides, imides, nitriles, and heterocycles.

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History

  • Published In Issue October 15, 2003
  • Received May 24, 2003

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