Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light

Carson D. Matier, Jonas Schwaben, Jonas C. Peters* and Gregory C. Fu*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States, Email: jpeterscaltech.edu, gcfucaltech.edu

C. D. Matier, J. Schwaben, J. C. Peteres, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 17707-17710.

DOI: 10.1021/jacs.7b09582

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Abstract

The selective mono-alkylation of aliphatic amines by unactivated, hindered halides is a challenge in organic synthesis. Primary aliphatic amines can be cleanly mono-alkylated by unactivated secondary alkyl iodides in the presence of visible light and a copper catalyst. The method operates under mild conditions (-10 °C) and displays good functional-group compatibility.

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proposed mechanism

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Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides

J. M. Ahn, J. C. Peters, G. C. Fu, J. Am. Chem. Soc., 2017, 139, 18101-18106.

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Key Words

amines

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ID: J48-Y2017