Synthesis 2017; 49(24): 5357-5363
DOI: 10.1055/s-0036-1588566
paper
© Georg Thieme Verlag Stuttgart · New York

A Rh(III)-Catalyzed Cascade C–H Functionalization/C(sp3)–C(sp3) Formation/Cyclization Reaction for the Synthesis of Isoquinolinedione Derivatives

Peng Bai
a   Department of Chemistry, Zhejiang University, Hangzhou 310028, P. R. of China   Email: huangzhizhen@zju.edu.cn
,
Kenneth L. Huang
b   Lakeside High School, 533 Blue Ridge Drive, Augusta, GA 30809, USA
,
Zhi-Zhen Huang*
a   Department of Chemistry, Zhejiang University, Hangzhou 310028, P. R. of China   Email: huangzhizhen@zju.edu.cn
› Author Affiliations
Financial support from the National Natural Science Foundation of China (No. 21372195) is gratefully acknowledged.
Further Information

Publication History

Received: 03 August 2017

Accepted after revision: 18 August 2017

Publication Date:
25 September 2017 (online)


Abstract

A cascade C–H functionalization/C(sp3)–C(sp3) formation/cyclization reaction of N-methoxybenzamides with diazomal­onates under rhodium(III) catalysis is developed for the efficient synthesis of isoquinolinedione derivatives. A plausible mechanism involving double migratory insertions of carbenes for the formation of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds by rhodium(III) catalysis is also proposed.

Supporting Information