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Investigation of Meyer–Schuster Rearrangement Promoted by a Samarium(III) Triflate/ N ‐Fluorobenzenesulfonimide Lewis Acid System
Author(s) -
Du Chuan,
Wang Xiaoyu,
Jin Shengfei,
Shi Hui,
Li Yangming,
Pang Yadong,
Liu Yang,
Cheng Maosheng,
Guo Chun,
Liu Yongxiang
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600124
Subject(s) - chemistry , trifluoromethanesulfonate , lewis acids and bases , medicinal chemistry , samarium , organic chemistry , catalysis
Abstract The acceleration effect from the addition of N ‐fluorobenzenesulfonimide (NFSI) to a samarium(III) triflate catalyzed Meyer–Schuster rearrangement under microwave irradiation was studied. Reaction rate plots indicate that the Sm(OTf) 3 /NFSI system is especially suitable for unreactive substrates towards the Meyer–Schuster rearrangement. The mechanism was probed by a crossover experiment using 18 O‐labeled substrates.