铜催化的 3-芳基吲哚的合成：通过 sp3 C-H 键活化，接着进行 C-C 和 C-O 键形成。

A copper-catalyzed synthesis of 3-aroylindoles via a sp3 C-H bond activation followed by C-C and C-O bond formation.

机构信息

Department of Chemistry, Indian Institute of Technology, Guwahati, Guwahati 781039, India.

出版信息

Org Lett. 2013 Apr 19;15(8):1802-5. doi: 10.1021/ol400692b. Epub 2013 Mar 29.

Abstract

An efficient Cu(I)-catalyzed synthesis of 3-aroylindoles has been achieved from o-alkynylated N,N-dimethylamines via a sp(3) C-H bond activation α to the nitrogen atom followed by an intramolecular nucleophilic attack with the alkyne using an aqueous solution of tert-butyl hydroperoxide (TBHP) as the oxidant. In this tandem catalytic synthesis of 3-aroylindoles both C-C and C-O bonds are installed at the expense of two sp(3) C-H bond cleavages.

摘要

一种高效的铜（I）催化合成 3-芳基吲哚的方法已经实现，该方法通过 sp(3) C-H 键活化α到氮原子，然后用叔丁基过氧化氢（TBHP）的水溶液作为氧化剂，与炔烃进行分子内亲核进攻，从邻炔基-N,N-二甲基胺出发。在这种 3-芳基吲哚的串联催化合成中，两个 sp(3) C-H 键的断裂导致了 C-C 和 C-O 键的同时形成。