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Visible‐Light‐Promoted Decarboxylative Giese Reactions of α‐Aryl Ethenylphosphonates and the Application in the Synthesis of Fosmidomycin Analogue
Author(s) -
Guo Ting,
Zhang Li,
Fang Yewen,
Jin Xiaoping,
Li Yan,
Li Ruifeng,
Li Xie,
Cen Wu,
Liu Xiaobo,
Tian Zongming
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.201701285
Subject(s) - chemistry , aryl , hydrolysis , alkylation , acrylate , combinatorial chemistry , phosphonate , carboxylic acid , visible spectrum , substrate (aquarium) , organic chemistry , catalysis , alkyl , polymer , physics , monomer , optoelectronics , oceanography , geology
An approach for the synthesis of α‐aryl alkylphosphonates based on visible‐light photocatalytic Giese reaction of α‐aryl vinylphosphonates with aliphatic carboxylic acids has been successfully developed. This protocol tolerates a wide range of functional groups and shows broad substrate scope with regard to both the carboxylic acid and vinylphosphonate components. With sequential Giese/hydrolysis reactions as the strategy, the oxo‐phosphonates could be easily accessible. The synthetic application of the hydroformylation reaction was demonstrated by the synthesis of the intermediate of α‐phenyl substituted fosmidomycin analogue. Furthermore, the competitive decarboxylative alkylation of vinylphosphonate and acrylate was also investigated.