%0 Journal Article
%@ 1523-7060
%A Pan, X
%A Curran, DP
%D 2014
%F pittir:25662
%J Organic Letters
%N 10
%P 2728 - 2731
%T Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
%U http://d-scholarship-dev.library.pitt.edu/25662/
%V 16
%X Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile. © 2014 American Chemical Society.