Literature DB >> 25504920

Redox-neutral α-allylation of amines by combining palladium catalysis and visible-light photoredox catalysis.

Jun Xuan1, Ting-Ting Zeng, Zhu-Jia Feng, Qiao-Hui Deng, Jia-Rong Chen, Liang-Qiu Lu, Wen-Jing Xiao, Howard Alper.   

Abstract

An unprecedented α-allylation of amines was achieved by combining palladium catalysis and visible-light photoredox catalysis. In this dual catalysis process, the catalytic generation of allyl radical from the corresponding π-allylpalladium intermediate was achieved without additional metal reducing reagents (redox-neutral). Various allylation products of amines were obtained in high yields through radical cross-coupling under mild reaction conditions. Moreover, the transformation was applied to the formal synthesis of 8-oxoprotoberberine derivatives which show potential anticancer properties.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic compounds; palladium; photochemistry; radicals; synthetic methods

Year:  2014        PMID: 25504920     DOI: 10.1002/anie.201409999

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  16 in total

1.  Detection of Fleeting Amine Radical Cations and Elucidation of Chain Processes in Visible-Light-Mediated [3 + 2] Annulation by Online Mass Spectrometric Techniques.

Authors:  Yi Cai; Jiang Wang; Yuexiang Zhang; Zhi Li; David Hu; Nan Zheng; Hao Chen
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

2.  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

3.  Photocatalytic Aminodecarboxylation of Carboxylic Acids.

Authors:  Simon B Lang; Kaitie C Cartwright; Richard S Welter; Theresa M Locascio; Jon A Tunge
Journal:  European J Org Chem       Date:  2016-06-19

4.  A visible-light activated secondary phosphine oxide ligand enabling Pd-catalyzed radical cross-couplings.

Authors:  Takahito Kuribara; Masaya Nakajima; Tetsuhiro Nemoto
Journal:  Nat Commun       Date:  2022-07-13       Impact factor: 17.694

5.  Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms.

Authors:  Simon B Lang; Kathryn M O'Nele; Justin T Douglas; Jon A Tunge
Journal:  Chemistry       Date:  2015-11-03       Impact factor: 5.236

Review 6.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

7.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 8.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

9.  Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.

Authors:  Xiao-Qiang Hu; Xiaotian Qi; Jia-Rong Chen; Quan-Qing Zhao; Qiang Wei; Yu Lan; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2016-04-06       Impact factor: 14.919

Review 10.  Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling.

Authors:  Mark D Levin; Suhong Kim; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-03       Impact factor: 14.553

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