One-Step Trimethylstannylation of Benzyl and Alkyl Halides

J Org Chem. 2016 Oct 7;81(19):9483-9488. doi: 10.1021/acs.joc.6b01883. Epub 2016 Sep 27.

Abstract

Trialkylstannanes are good leaving groups that have been used for the formation of carbon-metal bonds to electrode surfaces for analyses of single-molecule conductivity. Here, we report the multistep synthesis of two amide-containing compounds that are of interest in studies of molecular rectifiers. Each molecule has two trimethylstannyl units, one linked by a methylene and the other by an ethylene group. To account for the very different reactivities of the parent halides, a new methodology for one-step trimethylstannylation was developed and optimized.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.