Literature DB >> 29341489

Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3 )-H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates.

Maxim Ratushnyy1, Marvin Parasram1, Yang Wang1, Vladimir Gevorgyan1.   

Abstract

A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclizations; hydrogen-atom transfer; palladium; photochemistry; radicals

Mesh：

Substances：

Year:  2018        PMID： 29341489      PMCID： PMC5829020          DOI： 10.1002/anie.201712775

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


  52 in total

Review 1.  Catalysis of Radical Reactions: A Radical Chemistry Perspective.

Authors:  Armido Studer; Dennis P Curran
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-13       Impact factor: 15.336

2.  Palladium-catalyzed intramolecular iodine-transfer reactions in the presence of β-hydrogen atoms.

Authors:  Brendan M Monks; Silas P Cook
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-19       Impact factor: 15.336

3.  Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction.

Authors:  Jonathan Sperry; Yen-Cheng William Liu; Margaret A Brimble
Journal:  Org Biomol Chem       Date:  2009-10-07       Impact factor: 3.876

4.  Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors:  Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal:  Chem Rev       Date:  2016-12-02       Impact factor: 60.622

Review 5.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

6.  How Oliceridine (TRV-130) Binds and Stabilizes a μ-Opioid Receptor Conformational State That Selectively Triggers G Protein Signaling Pathways.

Authors:  Sebastian Schneider; Davide Provasi; Marta Filizola
Journal:  Biochemistry       Date:  2016-11-07       Impact factor: 3.162

7.  Gold-Catalyzed Photoredox C(sp(2)) Cyclization: Formal Synthesis of (±)-Triptolide.

Authors:  Alexandre Cannillo; Travis R Schwantje; Maxime Bégin; Francis Barabé; Louis Barriault
Journal:  Org Lett       Date:  2016-05-13       Impact factor: 6.005

8.  Directed β C-H Amination of Alcohols via Radical Relay Chaperones.

Authors:  Ethan A Wappes; Kohki M Nakafuku; David A Nagib
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

9.  Palladium-catalyzed carbohalogenation: bromide to iodide exchange and domino processes.

Authors:  Stephen G Newman; Jennifer K Howell; Norman Nicolaus; Mark Lautens
Journal:  J Am Chem Soc       Date:  2011-09-06       Impact factor: 15.419

10.  Stereoselective Radical Cyclization Cascades Triggered by Addition of Diverse Radicals to Alkynes To Construct 6(5)-6-5 Fused Rings.

Authors:  Lin Huang; Liu Ye; Xiao-Hua Li; Zhong-Liang Li; Jin-Shun Lin; Xin-Yuan Liu
Journal:  Org Lett       Date:  2016-10-04       Impact factor: 6.005
View more
  11 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

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.  C2-ketonylation of carbohydrates via excited-state palladium-catalyzed 1,2-spin-center shift.

Authors:  Gaoyuan Zhao; Upasana Mukherjee; Lin Zhou; Yue Wu; Wang Yao; Jaclyn N Mauro; Peng Liu; Ming-Yu Ngai
Journal:  Chem Sci       Date:  2022-05-11       Impact factor: 9.969

Review 5.  Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969

6.  Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Authors:  Leah M Stateman; Kohki M Nakafuku; David A Nagib
Journal:  Synthesis (Stuttg)       Date:  2018-02-12       Impact factor: 3.157

7.  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

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.  β C-H di-halogenation via iterative hydrogen atom transfer.

Authors:  Ethan A Wappes; Avassaya Vanitcha; David A Nagib
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

10.  A mild light-induced cleavage of the S-O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes.

Authors:  Maxim Ratushnyy; Monika Kamenova; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2018-07-25       Impact factor: 9.825
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.