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Bench‐Stable Electrophilic Fluorinating Reagents for Highly Selective Mono‐ and Difluorination of Silyl Enol Ethers
Author(s) -
Adachi Akiya,
Aikawa Kohsuke,
Ishibashi Yuichiro,
Nozaki Kyoko,
Okazoe Takashi
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101499
Subject(s) - silylation , reagent , enol , electrophile , electrophilic fluorination , chemistry , sulfonyl , combinatorial chemistry , organic chemistry , substrate (aquarium) , catalysis , alkyl , oceanography , geology
Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench‐stable electrophilic fluorinating reagents were synthesized as N ‐fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron‐withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base‐free conditions. Thus, both mono‐ and difluorinated target materials were prepared from the same substrate.