无金属条件下通过 PhI(OAc)2 介导的氧化 C-C 键形成反应合成 2-氧吲哚。

Metal-free synthesis of 2-oxindoles via PhI(OAc)2-mediated oxidative C–C bond formation.

出版信息

J Org Chem. 2014 Feb 7;79(3):1111-9. doi: 10.1021/jo4025539.

Abstract

The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp2)–C(sp2) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.

摘要

3-单官能化 2-氧吲哚 2 的这一系列化合物可通过苯胺 1 与二醋酸碘苯（PIDA）之间的高价碘介导的 C(sp2)-C(sp2)键形成反应，随后进行脱乙酰化反应，方便地合成。该无金属方法可直接得到重要的氧吲哚中间体，可应用于天然霍斯非林的全合成。