Nickel-Catalyzed Decarbonylative Thioetherification of Carboxylic Acids with Thiols

A nickel-catalyzed decarbonylative thioetherification of carboxylic acids with thiols was developed. Under the reaction conditions, benzoic acids, cinnamic acids, and benzyl carboxylic acids coupled with various thiols including both aromatic and aliphatic ones produce the corresponding thioethers i...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 13; pp. 8672 - 8684
Main Authors Xu, Tianhao, Zhou, Xingyu, Xiao, Xiong, Yuan, Yan, Liu, Long, Huang, Tianzeng, Li, Chunya, Tang, Zhi, Chen, Tieqiao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM
LIGANDS
SULFIDES
ESTERS
C-S
BOND FORMATION
SULFUR
THIOESTERS
THIOETHERS
AMIDES
Online AccessGet full text

Cover

More Information
Summary:A nickel-catalyzed decarbonylative thioetherification of carboxylic acids with thiols was developed. Under the reaction conditions, benzoic acids, cinnamic acids, and benzyl carboxylic acids coupled with various thiols including both aromatic and aliphatic ones produce the corresponding thioethers in up to 99% yields. Moreover, this reaction was applicable to the modification of bioactive molecules such as 3-methylflavone-8-carboxylic acid, probenecid, and flufenamic acid, and the synthesis of acaricide chlorbenside. These results well demonstrated the potential synthetic value of this new reaction in organic synthesis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00866