Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation

Author(s)
Billingsley, Kelvin L.; Buchwald, Stephen Leffler; Dufert, M. Alexander
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Abstract
The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimidazole, pyrazole, indole, oxindole, and azaindole halides under mild conditions in good to excellent yields. Additionally, the mechanism behind the inhibitory effect of unprotected azoles on Pd-catalyzed cross-coupling reactions is described based on evidence gained through experimental, crystallographic, and theoretical investigations.
Date issued
2013-08
URI
http://hdl.handle.net/1721.1/94501
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Düfert, M. Alexander, Kelvin L. Billingsley, and Stephen L. Buchwald. “Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation.” Journal of the American Chemical Society 135, no. 34 (August 28, 2013): 12877–12885.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126
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