Metal-Free Trifluoromethylation and Arylation of Alkenes: Domino Synthesis of Oxindole Derivatives

• Published in: Advanced synthesis & catalysis Vol. 356; no. 5; pp. 1021 - 1028
• Main Authors: Shi, Liangliang, Yang, Xiaobo, Wang, Yuyuan, Yang, Haijun, Fu, Hua
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 24.03.2014; WILEY‐VCH Verlag; Wiley
• Subjects: Alkenes; arylation; Chemistry; Chemistry, Applied; Chemistry, Organic; Contamination; Derivatives; domino reactions; Mediation; metal-free process; oxindole derivatives; Physical Sciences; Science & Technology; Sodium; Synthesis; Toxicology; Transition metals; trifluoromethylation; metal-free process; MEDIATED TRIFLUOROMETHYLATION; SANDMEYER TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; arylation; BORONIC ACIDS; oxindole derivatives; ACTIVATED ALKENES; COPPER-CATALYZED TRIFLUOROMETHYLATION; MECHANISTIC PATHWAYS; domino reactions; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; trifluoromethylation; BOND-FORMATION
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201300995

A novel, simple and highly efficient method for the synthesis of 3‐(trifluoromethyl)‐indolin‐2‐one derivatives has been developed. The protocol uses readily available N‐alkyl‐N‐phenylacrylamides as the starting materials, inexpensive and easily stored Langlois reagent (sodium trifluoromethanesulfinate) as the trifluoromethyl source, and iodobenzene diacetate [PhI(OAc)2] as the oxidant. The procedure involves a metal‐free domino trifluoromethylation and arylation of alkenes. The methods did not need mediation of any transition metal which avoided contaminations of toxic metals in the products.