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S ‐(Diethyl phosphonodifluoromethyl)Benzenesulfonothioate: A New Reagent for the Synthesis of SCF 2 PO(OEt) 2 ‐containing Molecules
Author(s) -
PetitCancelier Fabien,
François Benjamin,
Pannecoucke Xavier,
CouveBonnaire Samuel,
Besset Tatiana
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901454
Subject(s) - chemistry , reagent , combinatorial chemistry , thiol , molecule , disulfide bond , transformation (genetics) , radical , transition metal , organic chemistry , catalysis , biochemistry , gene
In this manuscript, the synthesis of an original SCF 2 PO(OEt) 2 ‐containing reagent was depicted. Thanks to the unique properties of this newly‐designed source, an unprecedented transformation with aldehydes was conducted under radical conditions, offering an access to value‐added fluoroalkylthio compounds. Preliminary mechanistic studies were conducted and supported a radical reaction mechanism. Remarkably, thiol and disulfide derivatives turned out to be suitable coupling partners in a transition metal free transformation towards the synthesis of difficult‐to‐synthesize unsymmetrical disulfides. Finally, the difunctionalization of 4‐phenyl‐butene was investigated using this reagent.