Electrochemical S-H and O-H insertion reactions from thiols or salicylic acids with diazo esters

An electrochemical carbenoid insertion reaction of diazo compounds into C-S and C-O bonds with electricity as the oxidant has been reported in this work. In this protocol, this transformation proceeded smoothly under mild conditions at room temperature in the absence of a catalyst and a ligand. In a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-10, Vol.2 (41), p.878-882
Main Authors: He, Zhiqin, Zhao, Wei, Li, Yufeng, Yu, Yang, Huang, Fei
Format: Article
Language:English
Subjects:
Catalysts
Chemical bonds
Electrochemistry
Esters
Insertion
Oxidants
Oxidizing agents
Room temperature
Thiols
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Summary:An electrochemical carbenoid insertion reaction of diazo compounds into C-S and C-O bonds with electricity as the oxidant has been reported in this work. In this protocol, this transformation proceeded smoothly under mild conditions at room temperature in the absence of a catalyst and a ligand. In addition, the yield of the S-H insertion product was up to 96% and the O-H product could be efficiently obtained in up to 80% yield. Of note is that this environmentally friendly strategy exhibited excellent applicability in gram-scale synthesis. An electrochemical insertion reaction of diazo compounds into C-S and C-O bonds with electricity as the oxidant under metal- and ligand-free conditions is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01273a