Controllable α- or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones

Murong Xu; Yang Yuan; Ye Wang; Qihai Tao; Chengyu Wang; Yanzhong Li

doi:10.1021/acs.orglett.9b02145

Controllable α- or β-Functionalization of α-Diazoketones with Aromatic Amides via Cobalt-Catalyzed C-H Activation: A Regioselective Approach to Isoindolinones

Org Lett. 2019 Aug 16;21(16):6264-6269. doi: 10.1021/acs.orglett.9b02145. Epub 2019 Jul 25.

Authors

Murong Xu¹, Yang Yuan¹, Ye Wang¹, Qihai Tao¹, Chengyu Wang², Yanzhong Li¹

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes School of Chemistry and Molecular Engineering , East China Normal University , 500 Dongchuan Road 200241 , Shanghai , China.
² School of Chemistry and Chemical Engineering , Linyi University , Shuangling Road , Linyi , Shandong 276000 , China.

PMID: 31343889
DOI: 10.1021/acs.orglett.9b02145

Abstract

Efficient procedures for the selective α- or β-functionalization of α-diazoketones with aromatic amides were developed by using a cobalt catalyst under ligand-free conditions. Normal α-functionalization of α-diazoketones was achieved via C(sp²)-H bond functionalization of aromatic amides in the presence of Co(acac)₂/TBHP. Interestingly, β-functionalization of α-diazoketones was realized with a Co(OAc)₂/AgOAc catalyst system. Further intramolecular cyclization afforded the desired isoindolinones in good to excellent yields.