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[3,3]‐Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides with Alkyl Nitriles
Author(s) -
Hu Mengjie,
He JiaNi,
Liu Yanping,
Dong Taotao,
Chen Mengyuan,
Yan Chao,
Ye Yulu,
Peng Bo
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901577
Subject(s) - chemistry , alkyl , aryl , electronegativity , sigmatropic reaction , deprotonation , group (periodic table) , functional group , medicinal chemistry , organic chemistry , ion , polymer
Herein we report the ortho ‐cyanoalkylation of aryl fluoroalkyl sulfoxides with alkyl nitriles. The reaction proceeds through an “assembly/deprotonation” triggered [3,3]‐rearrangement and allows the incorporation of two valuable functional groups including the cyano group and difluoromethylthio group into arenes. As a consequence, a wide range of ortho ‐cyanoalkylated difluoromethylthio arenes were produced with high efficiency under mild and environmentally friendly conditions. Remarkably, the reaction proceeds smoothly with the electron‐donating group substituted arenes which can be challenging to the reaction of non‐fluoroalkyl sulfoxides. This beneficial effect can be attributed to the unique electronegativity of fluoroalkyl substituents.