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Aerobic Visible‐Light Induced Intermolecular S−N Bond Construction: Synthesis of 1,2,4‐Thiadiazoles from Thioamides under Photosensitizer‐Free Conditions
Author(s) -
Zhuo Liang,
Xie Shihua,
Wang Hui,
Zhu Hongjun
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100440
Subject(s) - chemistry , photosensitizer , photochemistry , intermolecular force , thiadiazoles , radical , excited state , functional group , electron transfer , free base , combinatorial chemistry , medicinal chemistry , molecule , organic chemistry , physics , salt (chemistry) , nuclear physics , polymer
Aerobic visible‐light induced intermolecular S−N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4‐thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single‐electron‐transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4‐thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S−N bonds.