Selective Lithiation, Magnesiation, and Zincation of Unsymmetrical Azobenzenes Using Continuous Flow

Org Lett. 2017 Apr 7;19(7):1666-1669. doi: 10.1021/acs.orglett.7b00460. Epub 2017 Mar 15.

Abstract

A mild and general set of metalation procedures for the functionalization of unsymmetrical azobenzenes using a commercially available continuous-flow setup is reported. The metalations proceed with TMPLi under convenient conditions (0 °C, 20 s), and various classes of electrophiles can be used. With sensitive substrates, an in situ trapping metalation in which TMPLi is added to a mixture of the azobenzene and ZnCl2 or MgCl2·LiCl was very effective for achieving high yields.

Publication types

  • Research Support, Non-U.S. Gov't