Literature DB >> 27327358

Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition-Metal-Free Hydroamination and N-Arylation Reactions.

Jacob Davies1, Thomas D Svejstrup1, Daniel Fernandez Reina1, Nadeem S Sheikh2, Daniele Leonori1.   

Abstract

The development of photoredox reactions of aryloxy-amides for the generation of amidyl radicals and their use in hydroamination-cyclization and N-arylation reactions is reported. Owing to the ease of single-electron-transfer reduction of the aryloxy-amides, the organic dye eosin Y was used as the photoredox catalyst, which results in fully transition-metal-free processes. These transformations exhibit a broad scope, are tolerant to several important functionalities, and have been used in the late-stage modification of complex and high-value N-containing molecules.

Entities:  

Year:  2016        PMID: 27327358     DOI: 10.1021/jacs.6b04920

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  24 in total

1.  Merging Photoredox PCET with Nickel-Catalyzed Cross-Coupling: Cascade Amidoarylation of Unactivated Olefins.

Authors:  Shuai Zheng; Álvaro Gutiérrez-Bonet; Gary A Molander
Journal:  Chem       Date:  2019-01-03       Impact factor: 22.804

2.  Regioselective Radical Amino-Functionalizations of Allyl Alcohols via Dual Catalytic Cross-Coupling.

Authors:  Zuxiao Zhang; Duong T Ngo; David A Nagib
Journal:  ACS Catal       Date:  2021-03-03       Impact factor: 13.084

Review 3.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

4.  Directed Ni-Catalyzed Reductive Arylation of Aliphatic C-H Bonds.

Authors:  Zhi-Yun Liu; Silas P Cook
Journal:  Org Lett       Date:  2022-05-02       Impact factor: 6.072

5.  PCET-Enabled Olefin Hydroamidation Reactions with N-Alkyl Amides.

Authors:  Suong T Nguyen; Qilei Zhu; Robert R Knowles
Journal:  ACS Catal       Date:  2019-04-17       Impact factor: 13.084

6.  Allene Trifunctionalization via Amidyl Radical Cyclization and TEMPO Trapping.

Authors:  Robert M Ward; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2021-06-14       Impact factor: 4.354

Review 7.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

8.  Brønsted acid-promoted hydroamination of unsaturated hydrazones: access to biologically important 5-arylpyrazolines.

Authors:  Han He; Ning Xu; Honglin Zhang; Bin Chen; Zhengnan Hu; Kang Guo; Jianlin Chun; Shujun Cao; Yingguang Zhu
Journal:  RSC Adv       Date:  2021-05-11       Impact factor: 4.036

9.  A Simple and Broadly Applicable C-N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents.

Authors:  Xiaofeng Ma; Joshua J Farndon; Tom A Young; Natalie Fey; John F Bower
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

10.  Photoredox ketone catalysis for the direct C-H imidation and acyloxylation of arenes.

Authors:  Chandra Bhushan Tripathi; Tsuyoshi Ohtani; Michael T Corbett; Takashi Ooi
Journal:  Chem Sci       Date:  2017-06-05       Impact factor: 9.825

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