Nickel-Catalyzed C–S Reductive Cross-Coupling of Alkyl Halides with Arylthiosilanes toward Alkyl Aryl Thioethers

A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alk...

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Published inOrganic letters Vol. 24; no. 28; pp. 5115 - 5119
Main Authors Yang, Yu-Zhong, Li, Yang, Lv, Gui-Fen, He, De-Liang, Li, Jin-Heng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 22.07.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
THIOLS
DESIGN
SULFIDES
ARYLATION
CHLORIDES
BOND FORMATION
FACILE
EFFICIENT
DISULFIDES
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Summary:A nickel-catalyzed C–S reductive cross-coupling of alkyl halides with arylthiosilanes for producing alkyl aryl thioethers is developed. This reaction is initiated by umpolung transformations of arylthiosilanes followed by C–S reductive cross-coupling with alkyl halides to manage an electrophilic alkyl group onto the electrophilic sulfur atom and then construct a C­(sp3)–S bond, and features exquisite chemoselectivity, excellent tolerance of diverse functional groups, and wide applications for late-stage modification of biologically relevant molecules.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01954