Literature DB >> 25350690

Phenazinium salt-catalyzed aerobic oxidative amidation of aromatic aldehydes.

Dasheng Leow1.   

Abstract

Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catalytic loading (1-2 mol %). The reaction proceeds at ambient temperature and uses air as the sole oxidant. The operationally easy procedure provides an economical, green, and mild alternative for the formation of amide bonds.

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Year:  2014        PMID: 25350690     DOI: 10.1021/ol5029354

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  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

Review 2.  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

Review 3.  Photoredox-Catalyzed C-H Functionalization Reactions.

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

4.  Oxidative amidation of benzaldehyde using a quinone/DMSO system as the oxidizing agent.

Authors:  Itzel Mejía-Farfán; Manuel Solís-Hernández; Pedro Navarro-Santos; Claudia A Contreras-Celedón; Carlos Jesus Cortés-García; Luis Chacón-García
Journal:  RSC Adv       Date:  2019-06-10       Impact factor: 4.036

5.  Wavelength selective photoactivated autocatalytic oxidation of 5,12-dihydrobenzo[b]phenazine and its application in metal-free synthesis.

Authors:  Lei Bian; Jie Ma; Xiaotong Feng; Yuanhang Wang; Lizhi Zhao; Lei Zhao; Xiayan Wang; Guangsheng Guo; Qiaosheng Pu
Journal:  RSC Adv       Date:  2020-03-09       Impact factor: 4.036

6.  Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides.

Authors:  Mhairi Boyle; Keith Livingstone; Martyn C Henry; Jessica M L Elwood; J Daniel Lopez-Fernandez; Craig Jamieson
Journal:  Org Lett       Date:  2021-12-29       Impact factor: 6.005

7.  Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: synthesis of primary amides.

Authors:  Rohit B Kamble; Kishor D Mane; Bapurao D Rupanawar; Pranjal Korekar; A Sudalai; Gurunath Suryavanshi
Journal:  RSC Adv       Date:  2020-01-02       Impact factor: 4.036

8.  Exploring organic photosensitizers based on hemicyanine derivatives: a sustainable approach for preparation of amide linkages.

Authors:  Harnimarta Deol; Manoj Kumar; Vandana Bhalla
Journal:  RSC Adv       Date:  2018-09-05       Impact factor: 4.036

Review 9.  Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry.

Authors:  Michael K Bogdos; Emmanuel Pinard; John A Murphy
Journal:  Beilstein J Org Chem       Date:  2018-08-03       Impact factor: 2.883

Review 10.  Recent Advances in Visible-Light-Mediated Amide Synthesis.

Authors:  Bin Lu; Wen-Jing Xiao; Jia-Rong Chen
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411

  10 in total

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