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Co(acac)2/O2-Mediated Oxidative Isocyanide Insertion with 2-Aryl Anilines: Efficient Synthesis of 6-Amino Phenanthridine Derivatives

Author:
Zhu, Tong-Hao, Wang, Shun-Yi, Tao, Yang-Qing, Wei, Tian-Qi, Ji, Shun-Jun
Source:
Organic letters 2014 v.16 no.4 pp. 1260-1263
ISSN:
1523-7052
Subject:
carbon-hydrogen bond activation, chemical reactions, chemical structure, cobalt, homolytic cleavage, organic compounds, oxidants, oxygen
Abstract:
A novel and efficient protocol for the creation of 6-amino phenanthridine derivatives by Co(acac)₂-catalyzed isocyanide insertion with 2-aryl anilines under an O₂ atmosphere via homolytic aromatic substitution (HAS) type C–H functionalization has been developed. This reaction not only proceeds smoothly utilizing O₂ as the oxidant but also provides a new approach to construct phenanthridine derivatives utilizing readily available 2-aryl anilines with isocyanides instead of 2-isocyanobiaryls with different radical precursors.
Agid:
5788291