Construction of diverse C-S/C-Se bonds via nickel catalyzed reductive coupling employing thiosulfonates and a selenosulfonate under mild conditions

A nickel-catalyzed reductive cross coupling between organic iodides and thiosulfonates and a selenosulfonate under mild conditions is disclosed. This practical method provides a facile access to a series of unsymmetrical thioethers with low catalyst loading, good functional group tolerance, and exce...

Full description

Saved in:
Bibliographic Details
Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 5; pp. 1375 - 1382
Main Authors Liu, Yong, Xing, Shuya, Zhang, Jing, Liu, Wen, Xu, Yuenian, Zhang, Yan, Yang, Kefang, Yang, Lei, Jiang, Kezhi, Shao, Xinxin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.03.2022
Royal Society of Chemistry
Subjects
Catalysts
Chemistry
Chemistry, Organic
Cross coupling
Functional groups
Iodides
Nickel
Organic chemistry
Physical Sciences
Science & Technology
Selectivity
Thioethers
HALIDES
THIOLS
CARBON
REAGENTS
LIGANDS
SULFIDES
ARYL IODIDES
SULFUR
THIOARYLATION
CLEAVAGE
Online AccessGet full text

Cover

More Information
Summary:A nickel-catalyzed reductive cross coupling between organic iodides and thiosulfonates and a selenosulfonate under mild conditions is disclosed. This practical method provides a facile access to a series of unsymmetrical thioethers with low catalyst loading, good functional group tolerance, and excellent chemo-selectivity. Notably, the synthetic applications of the approach feature scaling-up of reactions, late-stage modification of pharmaceuticals, and preparation of various useful targeted compounds, including sulfoximine, bipyridine, and vortioxetine. Primary mechanistic studies showed that a radical pathway was involved. Moreover, diverse C-S/C-Se bond formations were achieved under mild reaction conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d1qo01873f