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Paper | Special issue | Vol 101, No. 2, 2020, pp.471-485
Published online, 2nd October, 2019
DOI: 10.3987/COM-19-S(F)30
Mechanistic Studies of Nickel(II)-Catalyzed Direct Alcoholysis of 8-Aminoquinoline Amides

Hiroyuki Morimoto,* Walaa Akkad, Toru Deguchi, and Takashi Ohshima*

*Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

This paper describes the mechanistic aspects of nickel(II)-catalyzed direct alcoholysis of 8-aminoquinoline amides. Kinetic experiments suggested that the nickel(II) catalyst existed in an oligomeric form in the resting state, and the 8-aminoquinoline generated after cleavage coordinated to the nickel(II) catalyst to decelerate the reaction. In addition, density functional theory calculations revealed that the reactions proceeded via the intermediate with N,N,O-tridentate coordination of 8-aminoquinoline amides to the nickel(II) metal center, and that the alcoholysis reaction did not involve deprotonation of the N–H bond of 8-aminoquinoline amides, in contrast to the proposed mechanism for C–H bond functionalization reactions of 8-aminoquinoline amides.