Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes
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MGB TFJ Org Lett 2011.pdf
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Author(s)
Beaver, Matthew G.
Jamison, Timothy F.
Date Issued
June 2011
Journal
Organic Letters
Publisher
American Chemical Society
Citation
Beaver, Matthew G., and Timothy F. Jamison. “Ni(II) Salts and 2-Propanol Effect Catalytic Reductive Coupling of Epoxides and Alkynes.” Organic Letters 13.15 (2011): 4140–4143. Web.
Version
Author's final manuscript
Abstract
A Ni-catalyzed reductive coupling of alkynes and epoxides using Ni(II) salts and simple alcohol reducing agents is described. Whereas previously reported conditions relied on Ni(cod)2 and Et3B, this system has several advantages including the use of air-stable and inexpensive Ni(II) precatalysts (e.g., NiBr2·3H2O) as the source of Ni(0) and simple alcohols (e.g., 2-propanol) as the reducing agent. Deuterium-labeling experiments are consistent with oxidative addition of an epoxide C–O bond that occurs with inversion of configuration.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ol201702a
