Organic Chemistry Portal



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:,

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

DOI: 10.1021/acs.joc.7b01202


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.

see article for more examples

Key Words

Ritter reaction, protected amines, PIDA, acetamides

ID: J42-Y2017