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A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination

Sheng Guo, Jeffrey C. Yang, Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

S. Guo, J. C. Yang, S. L. Buchwald, J. Am. Chem. Soc., 2018, 140, 15976-15984.

DOI: 10.1021/jacs.8b10564 (free Supporting Information)


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Abstract

The use of 1,2-benzisoxazole as a practical electrophilic primary amine source enables a mild and general copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines.

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Key Words

benzylic amines, CuH, dimethoxymethylsilane


ID: J48-Y2018