Literature DB >> 29451724

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

Maximilian Koy1, Frederik Sandfort1, Adrian Tlahuext-Aca1, Linda Quach1, Constantin G Daniliuc1, Frank Glorius1.   

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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2018        PMID： 29451724     DOI： 10.1002/chem.201800813

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  16 in total

1.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

2.  Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3 )-H Sites of Alcohols.

Authors:  Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-17       Impact factor: 15.336

3.  Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates.

Authors:  Wang Yao; Gaoyuan Zhao; Yue Wu; Lin Zhou; Upasana Mukherjee; Peng Liu; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2022-02-21       Impact factor: 15.419

4.  Visible Light Induced Brønsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones.

Authors:  Ziyan Zhang; Nikita Kvasovs; Anastasiia Dubrovina; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-23       Impact factor: 15.336

Review 5.  Visible Light-Induced Transition Metal Catalysis.

Authors:  Kelvin Pak Shing Cheung; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 72.087

6.  Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.

Authors:  Maxim Ratushnyy; Nikita Kvasovs; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-06       Impact factor: 15.336

7.  Transition-Metal-Catalyzed Alkyl Heck-Type Reactions.

Authors:  Daria Kurandina; Padon Chuentragool; Vladimir Gevorgyan
Journal:  Synthesis (Stuttg)       Date:  2019-02-07       Impact factor: 3.157

8.  Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates.

Authors:  Gaoyuan Zhao; Wang Yao; Jaclyn N Mauro; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

9.  Visible Light-Induced Pd-Catalyzed Alkyl-Heck Reaction of Oximes.

Authors:  Nikita Kvasovs; Valeriia Iziumchenko; Vitalii Palchykov; Vladimir Gevorgyan
Journal:  ACS Catal       Date:  2021-03-09       Impact factor: 13.084

10.  Three-component three-bond forming cascade via palladium photoredox catalysis.

Authors:  Peter Bellotti; Maximilian Koy; Christian Gutheil; Steffen Heuvel; Frank Glorius
Journal:  Chem Sci       Date:  2020-12-07       Impact factor: 9.825
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