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. 2018 Mar 26;24(18):4552-4555.
doi: 10.1002/chem.201800813. Epub 2018 Mar 9.

Palladium-Catalyzed Decarboxylative Heck-Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light

Maximilian Koy  1 , Frederik Sandfort  1 , Adrian Tlahuext-Aca  1 , Linda Quach  1 , Constantin G Daniliuc  1 , Frank Glorius  1
Affiliations

Palladium-Catalyzed Decarboxylative Heck-Type Coupling of Activated Aliphatic Carboxylic Acids Enabled by Visible Light

Maximilian Koy et al. Chemistry. .

Abstract

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(PPh3 )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.

Keywords: Heck-type coupling; carboxylic acids; decarboxylation; palladium; redox-active esters.

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