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Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides

Author(s)
Han, Chong; Buchwald, Stephen Leffler
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.

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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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Abstract
An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired β-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp[superscript 3])−C(sp[superscript 2]) bond formation.
Date issued
2009-05
URI
http://hdl.handle.net/1721.1/82067
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Han, Chong, and Stephen L. Buchwald. “Negishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides.” Journal of the American Chemical Society 131, no. 22 (June 10, 2009): 7532-7533.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126

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