C3-selective C-H thiolation of quinolines via an N-arylmethyl activation strategy

An N-arylmethyl activation strategy has been developed to solve the challenging problems associated with the direct C3-H thiolation reaction of quinolines, including trifluoromethyl thiolation, aryl thiolation, alkyl thiolation and phenyl selenylation. The relevant theoretical calculations of the lo...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 9; pp. 2324 - 2331
Main Authors Li, Shun, Tang, Juan, Fu, Yi-Hua, Zheng, Xue-Li, Yuan, Mao-Lin, Li, Rui-Xiang, Su, Zhi-Shan, Fu, Hai-Yan, Chen, Hua
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 02.05.2023
Royal Society of Chemistry
Subjects
Biological activity
Chemistry
Chemistry, Organic
Functional groups
Organic chemistry
Organic compounds
Physical Sciences
Quinoline
Quinolines
Science & Technology
Substrates
FUNCTIONALIZATION
BROMINATION
ALKYL RADICALS
ARYLATION
SULFENYLATION
SUBSTITUENT CONSTANTS
AROMATICS
HALOGENATION
PYRIDINES
CATALYST
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Summary:An N-arylmethyl activation strategy has been developed to solve the challenging problems associated with the direct C3-H thiolation reaction of quinolines, including trifluoromethyl thiolation, aryl thiolation, alkyl thiolation and phenyl selenylation. The relevant theoretical calculations of the local nucleophilic indices of quinolinium salts were performed to rationalize the site-selectivity. This metal-free protocol features a broad substrate scope, generally high yield, and good functional group compatibility. The practicality and potential application of this protocol were further demonstrated by a facile scale-up reaction and the late-stage thiolation of a wide range of quinoline-based biologically active complex molecules.
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/d3qo00244f