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Alternative Palladium‐Catalyzed Vinylic C−H Difluoroalkylation of Ketene Dithioacetals Using Bromodifluoroacetate Derivatives
Author(s) -
Tian Shuangquan,
Song Xiaoning,
Zhu Dongsheng,
Wang Mang
Publication year - 2018
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.201701554
Subject(s) - ketene , chemistry , palladium , olefin fiber , catalysis , double bond , medicinal chemistry , organic chemistry , combinatorial chemistry
A palladium‐catalyzed cross‐coupling of α‐oxo ketene dithioacetals and bromodifluoroacetate derivatives has been developed for the synthesis of a class of CF 2 ‐containing tetra‐substituted olefins, which has potential to extend to drug design and material application. The process is proposed to involve two single electron transfer processes accompanied by an alternative loop from palladium(0) to palladium(I), likely due to unique structural properties of ketene dithioacetals with β,β‐dialkylthiol substituents on the olefin double bond.