AgI‐Promoted Cascade for Difluoromethylation of Activated Alkenes to Difluoromethylated Oxindoles. Issue 22 (14th July 2016)

• Record Type: Journal Article
• Authors: Wang, Xinglu; Wan, Wen; Chen, Yunrong; Li, Jialiang; Jiang, Haizhen; Wang, Yong; Deng, Hongmei; Hao, Jian
• Is Part Of: European journal of organic chemistry. Issue 22(2016)
• Page Start: 3773
• Page End: 3779
• Publication Date: 2016-07-14
• Subjects: Nitrogen heterocycles -- Domino reactions -- Fluorine -- Radicals -- Silver; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201600461
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A simple Ag I ‐mediated direct difluoromethylation reaction of activated alkenes by using TMSCF2 COOEt (TMS = trimethylsilyl) under mild reaction conditions has been described. This reaction tolerates a variety of functional groups and allows for a highly efficient synthesis of various difluoro‐containing oxindoles. Mechanistic investigations indicate that a difluoromethyl radical initiated the cascade sequence by undergoing an addition reaction to the alkene. Abstract : A highly efficient synthesis of various difluoro‐containing oxindoles has been achieved by using the described Ag I ‐mediated direct difluoromethylation reaction of activated alkenes.