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Metal-Free Synthesis of 2-Oxindoles via PhI(OAc)2-Mediated Oxidative C-C Bond Formation

Jinglei Lv, Daisy Zhang-Negrerie, Jun Deng, Yunfei Du* and Kang Zhao*

*School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, People’s Republic of China, Email: duyunfeiertju.edu.cn, kangzhaotju.edu.cn

J. Lv, D. Zhang-Negrerie, J. Deng, Y. Du, K. Zhao, J. Org. Chem., 2014, 79, 1111-1119.

DOI: 10.1021/jo4025539 (free Supporting Information)


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Abstract

3-Monofunctionalized 2-oxindoles were conveniently synthesized from reactions between an anilide and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp2)–C(sp2) bond formation followed by a subsequent deacylation. This metal-free method provides direct access to interesting oxindole intermediates, as exemplified by the total synthesis of horsfiline.

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Key Words

oxindoles, PIDA


ID: J42-Y2014