Premium
Palladium‐Catalyzed Decarboxylative Heck‐Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light
Author(s) -
Koy Maximilian,
Sandfort Frederik,
TlahuextAca Adrian,
Quach Linda,
Daniliuc Constantin G.,
Glorius Frank
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800813
Subject(s) - decarboxylation , palladium , catalysis , chemistry , alkyl , radical , carboxylic acid , photocatalysis , photochemistry , visible spectrum , organic chemistry , materials science , optoelectronics
The palladium‐catalyzed coupling reaction of N ‐hydroxyphthalimide esters and styrenes to deliver exclusively ( E )‐substituted olefins under irradiation with visible light is reported. This method tolerates N ‐hydroxyphthalimide esters derived from primary, secondary, tertiary as well as benzylic carboxylic acids. Notably, Pd(PPh 3 ) 4 is employed as an inexpensive palladium source and no addition of base or classical photocatalyst is required. Mechanistic studies suggest a light‐mediated single‐electron reduction of the activated acid by a photoexcited palladium(0) species to access alkyl radicals through decarboxylation.