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Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides

Pan, X and Curran, DP (2014) Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides. Organic Letters, 16 (10). 2728 - 2731. ISSN 1523-7060

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Abstract

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.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Pan, X
Curran, DPcurran@pitt.eduCURRAN
Date: 16 May 2014
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 16
Number: 10
Page Range: 2728 - 2731
DOI or Unique Handle: 10.1021/ol5010164
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Catalysis; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism; Sulfides--chemical synthesis; Sulfides--chemistry; Tetrazoles--chemical synthesis; Tetrazoles--chemistry
PubMed ID: 24802672
Date Deposited: 20 Jul 2015 16:01
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/25662

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