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A Palladium‐Catalyzed Decarboxylative Heck‐Type Reaction of Disubstituted Vinylphosphonates in the Stereoselective Synthesis of Trisubstituted Vinylphosphonates
Author(s) -
Ren Linjing,
Ran Maogang,
He Jiaxin,
Xiang Dan,
Chen Feng,
Liu Peijun,
He Chunyang,
Yao Qiuli
Publication year - 2019
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.201900810
Subject(s) - stereoselectivity , chemistry , palladium , catalysis , heck reaction , organic chemistry , combinatorial chemistry
We describe a highly stereoselective and atomically economical approach for the preparation of trisubstituted vinylphosphonates through palladium‐catalyzed decarboxylative Heck‐type reactions of vinylphosphonates. Excellent E/Z selectivity was achieved mostly with E ‐isomers; this was difficult to achieve via traditional methods. Oxygen in the air was the sole oxidant, and this minimizes the use of high‐loading silver or other species. This work is the first example to synthesize vinylphosphonates via a catalyzed decarboxylative Heck‐type reaction.