Triphenylbismuth Dichloride‐Mediated Conversion of Thioamides to Nitriles

Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process wa...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2019; no. 25; pp. 4043 - 4045
Main Authors Gopi, Elumalai, Gravel, Edmond, Doris, Eric
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 07.07.2019
Wiley Subscription Services, Inc
Wiley-VCH Verlag
Subjects
Aliphatic compounds
Bismuth
Chemical Sciences
Chemistry
Chemistry, Organic
Cyanamides
Dehydrosulfurization
Dichlorides
Nitriles
Physical Sciences
Science & Technology
Synthesis design
Thioamides
Thiocyanates
Triethylamine
OXIDATION
PHENYLATION
Thioamides
Synthesis design
CARBOXYLATES
PRIMARY AMIDES
ARYLATION
Bismuth
CHEMISTRY
Nitriles
PENTAVALENT ORGANOBISMUTH REAGENTS
Dehydrosulfurization
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Summary:Thioamides were efficiently converted to nitriles using the pentavalent triphenylbismuth dichloride in combination with triethylamine. The reaction involved the dehydrosulfurization of primary thioamides to afford substituted aromatic or aliphatic nitriles in good to excellent yields. The process was also successfully extended to the synthesis of cyanamides starting from the corresponding thioureas and of thiocyanates from dithiocarbamates. Thioamides, thioureas, and dithiocarbamates were efficiently converted to nitriles, cyanamides, and thiocyanates, respectively, using pentavalent triphenylbismuth dichloride in combination with triethylamine in dichloromethane.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900563