Literature DB >> 23915114

Ruthenium-catalyzed redox-neutral and single-step amide synthesis from alcohol and nitrile with complete atom economy.

Byungjoon Kang1, Zhenqian Fu, Soon Hyeok Hong.   

Abstract

A completely atom-economical and redox-neutral catalytic amide synthesis from an alcohol and a nitrile is realized. The amide C-N bond is efficiently formed between the nitrogen atom of nitrile and the α-carbon of alcohol, with the help of an N-heterocyclic carbene-based ruthenium catalyst, without a single byproduct. A utility of the reaction was demonstrated by synthesizing (13)C or (15)N isotope-labeled amides without involvement of any separate reduction and oxidation step.

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Year:  2013        PMID: 23915114     DOI: 10.1021/ja404695t

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


  6 in total

1.  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

2.  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

3.  New Furan and Cyclopentenone Derivatives from the Sponge-Associated Fungus Hypocrea Koningii PF04.

Authors:  Li-Jian Ding; Bin-Bin Gu; Wei-Hua Jiao; Wei Yuan; Ying-Xin Li; Wei-Zhuo Tang; Hao-Bing Yu; Xiao-Jian Liao; Bing-Nan Han; Zhi-Yong Li; Shi-Hai Xu; Hou-Wen Lin
Journal:  Mar Drugs       Date:  2015-08-26       Impact factor: 5.118

4.  Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.

Authors:  Kenneth E Schwieter; Bo Shen; Jessica P Shackleford; Matthew W Leighty; Jeffrey N Johnston
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005

5.  Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes.

Authors:  Thilo Krause; Sabrina Baader; Benjamin Erb; Lukas J Gooßen
Journal:  Nat Commun       Date:  2016-06-10       Impact factor: 14.919

6.  Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes.

Authors:  Sheng Xie; Yang Zhang; Olof Ramström; Mingdi Yan
Journal:  Chem Sci       Date:  2015-10-22       Impact factor: 9.825

  6 in total

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