Palladium‐Catalyzed Decarboxylative Heck‐Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light | Zendy

Koy Maximilian | Zendy; Sandfort Frederik | Zendy; TlahuextAca Adrian | Zendy; Quach Linda | Zendy; Daniliuc Constantin G. | Zendy; Glorius Frank | Zendy

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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.

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