Literature DB >> 32155303

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

Maxim Ratushnyy1,2, Nikita Kvasovs1,2, Sumon Sarkar1,2, Vladimir Gevorgyan1,2.   

Abstract

A mild visible-light-induced Pd-catalyzed intramolecular C-H arylation of amides is reported. The method operates by cleavage of a C(sp2 )-O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  homolysis; light-mediated reactions; palladium; radicals; triflates

Year:  2020        PMID： 32155303      PMCID： PMC7446712          DOI： 10.1002/anie.201915962

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


  65 in total

1.  General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

Authors:  Padon Chuentragool; Marvin Parasram; Yi Shi; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2018-02-07       Impact factor: 15.419

2.  Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles.

Authors:  James R Donald; Richard J K Taylor; Wade F Petersen
Journal:  J Org Chem       Date:  2017-09-28       Impact factor: 4.354

3.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

4.  Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy.

Authors:  Qianjia Yuan; Matthew S Sigman
Journal:  Chemistry       Date:  2019-07-26       Impact factor: 5.236

Review 5.  Catalysis with Palladium Complexes Photoexcited by Visible Light.

Authors:  Padon Chuentragool; Daria Kurandina; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-24       Impact factor: 15.336

6.  General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols.

Authors:  Marvin Parasram; Padon Chuentragool; Yang Wang; Yi Shi; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2017-10-12       Impact factor: 15.419

7.  Synthesis of All-Carbon Quaternary Centers by Palladium-Catalyzed Olefin Dicarbofunctionalization.

Authors:  Maximilian Koy; Peter Bellotti; Felix Katzenburg; Constantin G Daniliuc; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-09       Impact factor: 15.336

8.  Guided desaturation of unactivated aliphatics.

Authors:  Ana-Florina Voica; Abraham Mendoza; Will R Gutekunst; Jorge Otero Fraga; Phil S Baran
Journal:  Nat Chem       Date:  2012-07-08       Impact factor: 24.427

9.  Irradiation-induced palladium-catalyzed decarboxylative desaturation enabled by a dual ligand system.

Authors:  Wan-Min Cheng; Rui Shang; Yao Fu
Journal:  Nat Commun       Date:  2018-12-06       Impact factor: 14.919

10.  Catalytic β C-H amination via an imidate radical relay.

Authors:  Leah M Stateman; Ethan A Wappes; Kohki M Nakafuku; Kara M Edwards; David A Nagib
Journal:  Chem Sci       Date:  2019-01-17       Impact factor: 9.825
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  9 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.  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 3.  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

4.  Contemporary methods for generation of aryl radicals.

Authors:  Nikita Kvasovs; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2021-03-01       Impact factor: 54.564

5.  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

6.  Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism.

Authors:  Lin Huang; Alessandro Bismuto; Simon A Rath; Nils Trapp; Bill Morandi
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-25       Impact factor: 15.336

7.  Selective desaturation of amides: a direct approach to enamides.

Authors:  Xinwei Li; Zengrui Cheng; Jianzhong Liu; Ziyao Zhang; Song Song; Ning Jiao
Journal:  Chem Sci       Date:  2022-07-06       Impact factor: 9.969

8.  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

Review 9.  Isoindolinone Synthesis via One-Pot Type Transition Metal Catalyzed C-C Bond Forming Reactions.

Authors:  Risto Savela; Carolina Méndez-Gálvez
Journal:  Chemistry       Date:  2021-02-02       Impact factor: 5.236
  9 in total

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