Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives

Kensuke Kiyokawa*, Tomoki Watanabe, Laura Fra, Takumi Kojima and Satoshi Minakata*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: kiyokawachem.eng.osaka-u.ac.jp, minakatachem.eng.osaka-u.ac.jp

K. Kiyokawa, T. Watanabe, L. Fra, T. Kojima, S. Minakata, J. Org. Chem., 2017, 82, 11711-11720.

DOI: 10.1021/acs.joc.7b01202

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Abstract

The Ritter reaction is a reliable approach for preparing α-tertiary amine derivatives, but typical methods suffer from harsh reaction conditions and the use of strong acids. A decarboxylative Ritter-type amination of carboxylic acids bearing an α-quaternary carbon center using a combination of PhI(OAc)₂ and molecular iodine (I₂) provides the corresponding α-tertiary amine derivatives at ambient temperature on the benchtop with a fluorescent light.

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Key Words

Ritter reaction, protected amines, PIDA, acetamides

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ID: J42-Y2017