Relay C(sp3)-H bond trifluoromethylthiolation and amidation by visible light photoredox catalysis

Selective functionaliz0ation of C(sp 3 )–H bonds is a straightforward and practical method to construct complex molecule skeletons. In this field, direct transformation of unactivated C(sp 3 )–H bonds into C(sp 3 )–SCF 3 architectures is still a great challenge. We report a highly selective trifluor...

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Bibliographic Details
Published in:Science China. Chemistry 2024-11, Vol.67 (11), p.3844-3850
Main Authors: Liu, Junheng, Yang, Suqi, Yao, Shunruo, Zhu, Chengjian, Liu, Yong, Li, Weipeng, Xie, Jin
Format: Article
Language:English
Subjects:
Additives
Catalysis
Chemical bonds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chromatography
Electron transfer
Hydrogen atoms
Hydrogen bonds
Laboratories
Light emitting diodes
Pharmaceutical industry
Photocatalysis
Photoredox catalysis
Solvents
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Summary:Selective functionaliz0ation of C(sp 3 )–H bonds is a straightforward and practical method to construct complex molecule skeletons. In this field, direct transformation of unactivated C(sp 3 )–H bonds into C(sp 3 )–SCF 3 architectures is still a great challenge. We report a highly selective trifluoromethylthiolation of unactivated aliphatic C(sp 3 )–H bonds by combination of proton-coupled electron transfer (PCET) and hydrogen atom transfer (HAT) strategy. A wide range of structurally diverse alkyl trifluoromethyl sulfides are obtained. Furthermore, the use of two different photocatalysts can realize an unprecedented trifluoromethylthiolation and amidation cascade of different C(sp 3 )–H bonds. It can afford a good access to bifunctionalized molecules in synthetically useful yields.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-024-2259-7