Literature DB >> 23560642

Highly practical synthesis of nitriles and heterocycles from alcohols under mild conditions by aerobic double dehydrogenative catalysis.

Weiyu Yin1, Chengming Wang, Yong Huang.   

Abstract

A mild, aerobic, catalytic process for obtaining nitriles directly from alcohols and aqueous ammonia is described. The reaction proceeds via a dehydrogenation cascade mediated by catalytic CuI, bpy, and TEMPO in the presence of O2. The substrate scope is broad including various functionalized aromatic and aliphatic alcohols. This protocol enabled the one-pot synthesis of various biaryl heterocycles directly from commercially available alcohols.

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Year:  2013        PMID: 23560642     DOI: 10.1021/ol400459y

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


  12 in total

1.  Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature.

Authors:  Jinho Kim; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-07-05       Impact factor: 13.084

2.  Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile.

Authors:  Wandi Zhang; Christopher W Haskins; Yang Yang; Mingji Dai
Journal:  Org Biomol Chem       Date:  2014-12-07       Impact factor: 3.876

Review 3.  Practical aerobic oxidations of alcohols and amines with homogeneous copper/TEMPO and related catalyst systems.

Authors:  Bradford L Ryland; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

4.  Practical Synthesis of Amides via Copper/ABNO-Catalyzed Aerobic Oxidative Coupling of Alcohols and Amines.

Authors:  Susan L Zultanski; Jingyi Zhao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2016-05-16       Impact factor: 15.419

5.  Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes.

Authors:  Richard Y Liu; Minwoo Bae; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-01-29       Impact factor: 15.419

6.  Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-11-01       Impact factor: 13.084

7.  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

8.  Controllable cyanation of carbon-hydrogen bonds by zeolite crystals over manganese oxide catalyst.

Authors:  Liang Wang; Guoxiong Wang; Jian Zhang; Chaoqun Bian; Xiangju Meng; Feng-Shou Xiao
Journal:  Nat Commun       Date:  2017-05-15       Impact factor: 14.919

9.  Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia.

Authors:  Jan Vilím; Tanja Knaus; Francesco G Mutti
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-08       Impact factor: 15.336

10.  NH3⋅H2O: The Simplest Nitrogen-Containing Ligand for Selective Aerobic Alcohol Oxidation to Aldehydes or Nitriles in Neat Water.

Authors:  Guofu Zhang; Danting Ma; Yiyong Zhao; Guihua Zhang; Guangyao Mei; Jinghui Lyu; Chengrong Ding; Shang Shan
Journal:  ChemistryOpen       Date:  2018-11-13       Impact factor: 2.911

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