Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

Kanako Nozawa-Kumada; Yuta Matsuzawa; Kanako Ono; Masanori Shigeno; Yoshinori Kondo

doi:10.1039/d1cc02870g

Copper-catalyzed aerobic double functionalization of benzylic C(sp³)-H bonds for the synthesis of 3-hydroxyisoindolinones

Chem Commun (Camb). 2021 Sep 7;57(69):8604-8607. doi: 10.1039/d1cc02870g. Epub 2021 Aug 9.

Authors

Kanako Nozawa-Kumada¹, Yuta Matsuzawa, Kanako Ono, Masanori Shigeno, Yoshinori Kondo

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan. kanako.kumada.d1@tohoku.ac.jp yoshinori.kondo.a7@tohoku.ac.jp.

PMID: 34368822
DOI: 10.1039/d1cc02870g

Abstract

A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp³)-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp³)-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp³)-H bonds and shows excellent functional group tolerance.