Silver-Catalyzed C(sp2)–H Functionalization/C–O Cyclization Reaction at Room Temperature

Silver-catalyzed C(sp2)–H functionalization/C–O cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)2S2O8 oxidan...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-01, Vol.80 (2), p.911-919
Main Authors: Dai, Jian-Jun, Xu, Wen-Tao, Wu, Ya-Dong, Zhang, Wen-Man, Gong, Ying, He, Xia-Ping, Zhang, Xin-Qing, Xu, Hua-Jian
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Kinetics
Lactones - chemistry
Molecular Structure
Silver - chemistry
Silver Nitrate - chemistry
Temperature
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Summary:Silver-catalyzed C(sp2)–H functionalization/C–O cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)2S2O8 oxidant in CH2Cl2/H2O solvent, various lactones are obtained in good to excellent yields. A kinetic isotope effect (KIE) study indicates that the reaction may occur via a radical process.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5024238