Synthesis of Dichlorocyanomethyl‐Functionalized Oxindoles by Cascade Reactions Initiated by Copper(I)‐Catalytically Generated Dichlorocyanomethyl Radical. Issue 22 (1st October 2020)

• Record Type: Journal Article
• Authors: Che, Fengrui; Zhong, Jiangbin; Yu, Linhan; Ma, Chaopeng; Yu, Chunzheng; Wang, Maorong; Hou, Zhichen; Zhang, Yuexia
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 22(2020)
• Page Start: 5020
• Page End: 5025
• Publication Date: 2020-10-01
• Subjects: trichloroacetonitrile -- oxindoles -- single-electron transfer -- N-arylacrylamides -- radical; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000600
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An efficient and convenient protocol for synthesis of dichlorocyanomethyl‐functionalized oxindoles through the cascade reactions of dichlorocyanomethyl radical with N ‐arylacrylamides is reported. The electrophilic dichlorocyanomethyl radical, which is generated from readily available trichloroacetonitrile via a copper‐catalyzed single‐electron transfer (SET) process, undergoes radical addition with the electron‐deficient C=C bonds of N ‐arylacrylamides, followed by intramolecular cyclization, to provide dichlorocyanomethyl‐functionalized oxindoles. No external oxidant is needed in this transformation. Abstract :