Chemoselective Chan–Lam Coupling Reactions between Benzimidazoline-2-thiones and Arylboronic Acids

An efficient Chan–Lam-type methodology for the selective synthesis of S-arylbenzimidazoles and N,S-diarylbenzimidazoles was developed. The selectivity was controlled by varying the amount of the catalyst Cu­(OAc)2·H2O, temperature, and solvent switching. These transformations feature a simple protoc...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 18; pp. 11524 - 11532
Main Authors Liu, Xing, Dong, Zhi-Bing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.09.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BORONIC ACIDS
S-ARYLATION
ORGANOBORONIC ACIDS
P-ARYLTHIO CINNAMIDES
C-N
BOND FORMATION
COPPER
SULFUR
ADHESION MOLECULE-1 INTERACTION
BENZIMIDAZOLES
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Summary:An efficient Chan–Lam-type methodology for the selective synthesis of S-arylbenzimidazoles and N,S-diarylbenzimidazoles was developed. The selectivity was controlled by varying the amount of the catalyst Cu­(OAc)2·H2O, temperature, and solvent switching. These transformations feature a simple protocol, broad functional group tolerance, high selectivity, and good to excellent yields. It is noteworthy that these reactions represent the first examples of the application of the selective Chan–Lam coupling.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01370