AgI‐Promoted Difluoromethylation of Isocyanides To Give Difluoromethylated Phenanthridines. Issue 22 (9th June 2017)

• Record Type: Journal Article
• Authors: Wan, Wen; Xu, Xiaochen; Chen, Yunrong; Jiang, Haizhen; Wang, Yong; Deng, Hongmei; Hao, Jian
• Is Part Of: European journal of organic chemistry. Issue 22(2017)
• Page Start: 3145
• Page End: 3151
• Publication Date: 2017-06-09
• Subjects: Fluorinated compounds -- Fluorine -- Radicals -- Cyclization -- Isocyanides -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700470
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An Ag I ‐mediated ethoxycarbonyldifluoromethylation of isocyanides has been developed. This radical cascade reaction involves the addition of difluoromethylene radical to the isocyanide functionality, and subsequent homolytic aromatic substitution to give difluoromethylated phenanthridines with a good functional‐group tolerance. Abstract : A convenient synthesis of ethoxycarbonyldifluoromethylated phenanthridines has been developed. The reaction involves an Ag I ‐mediated cascade gem ‐difluoromethylenation/cyclization of isocyanides with Me3 SiCF2 CO2 Et under mild reaction conditions.