Rhodium(III)‐Catalyzed Direct C‐H Alkylation of 2‐Aryl‐1, 2, 3‐triazole N‐Oxides with Maleimides. Issue 48 (4th December 2018)

• Record Type: Journal Article
• Authors: Zhao, Juanli; Pi, Chao; You, Chang; Wang, Yong; Cui, Xiuling; Wu, Yangjie
• Is Part Of: European journal of organic chemistry. Issue 48(2018)
• Page Start: 6919
• Page End: 6923
• Publication Date: 2018-12-04
• Subjects: Alkylation -- High atom efficiency -- Regioselectivity -- Rhodium catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801353
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient rhodium(III)‐catalyzed direct C‐H ortho ‐alkylation of 2‐aryl‐1, 2, 3‐triazole N ‐oxides has been developed using maleimides as the alkylation reagent. This protocol displays good functional group tolerance, high atom efficiency and avoids the external oxidant. Only mono‐substituted products were obtained. Based on the results of deuterium exchange experiments, the N ‐oxide group plays an important role to improve the regioselectivity by increasing the steric hindrance. Abstract : A novel strategy for rhodium‐catalyzed direct C‐H ortho ‐alkylation of 2‐aryl‐1, 2, 3‐triazole N ‐oxides with maleimides was reported. It proceeds with high atom efficiency, free external oxidant, excellent regioselectivity, and convenient on a gram‐scale.