Tandem radical cyclization to construct poly-brominated 2-oxindoles. Issue 36 (6th September 2017)

• Record Type: Journal Article
• Authors: Chen, Fengjuan; Wang, Yajun; Zhao, Shijun; Jiang, Wei; Huo, Congde
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 36(2017)
• Page Start: 7710
• Page End: 7714
• Publication Date: 2017-09-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01859b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A metal-free aerobic way to construct tribromomethylated poly-brominated 2-oxindoles from reaction of N -arylacrylamides with CBr4 via a tandem radical cyclization process was discovered. The formation of the 1, 1-dibromoolefin derivatives was also realized at higher temperature. Abstract : Catalytic amounts of TBHP (15 mol%) promoted tribromomethylation of activated alkenes has been developed. This method provided a metal-free aerobic way to construct tribromomethylated 2-oxindoles from the reaction of readily available N -arylacrylamides with CBr4 via a proposed tandem radical cyclization process. Air is used as an efficient terminal oxidant in this transformation. The formation of 1, 1-dibromoolefin derivatives was also realized at higher temperature under neat conditions.