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

Identifieur interne : 001F01 ( Main/Exploration ); précédent : 001F00; suivant : 001F02

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

Auteurs : Xiangcheng Pan [États-Unis] ; Dennis P. Curran

Source :

Organic letters [ 1523-7052 ] ; 2014.

RBID : pubmed:24802672

Descripteurs français

KwdFr :
- Catalyse, Spectroscopie par résonance magnétique, Structure moléculaire, Stéréoisomérie, Sulfures (), Sulfures (synthèse chimique), Tétrazoles (), Tétrazoles (synthèse chimique).
MESH :
- synthèse chimique : Sulfures, Tétrazoles.
- Catalyse, Spectroscopie par résonance magnétique, Structure moléculaire, Stéréoisomérie, Sulfures, Tétrazoles.

English descriptors

KwdEn :
- Catalysis, Magnetic Resonance Spectroscopy, Molecular Structure, Stereoisomerism, Sulfides (chemical synthesis), Sulfides (chemistry), Tetrazoles (chemical synthesis), Tetrazoles (chemistry).
MESH :
- chemical , chemical synthesis : Sulfides, Tetrazoles.
- chemical , chemistry : Sulfides, Tetrazoles.
- Catalysis, Magnetic Resonance Spectroscopy, Molecular Structure, Stereoisomerism.

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.

DOI: 10.1021/ol5010164
PubMed: 24802672

Affiliations:

États-Unis

Le document en format XML

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<front><div type="abstract" xml:lang="en">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.</div>
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Neutral sulfur nucleophiles: synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides.

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

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

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