Literature DB >> 23545123

Facile Cu(I)-catalyzed oxidative coupling of anilines to azo compounds and hydrazines with diaziridinone under mild conditions.

Yingguang Zhu1, Yian Shi.   

Abstract

A mild and highly efficient Cu(I)-catalyzed oxidative coupling of anilines is described. Various primary and secondary anilines can be efficiently coupled under mild conditions to the corresponding azo compounds and hydrazines in high yields. This method provides a direct and practical access to these compounds and is also amenable to gram scale with no special precautions to exclude air or moisture.

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Year:  2013        PMID: 23545123      PMCID: PMC3717407          DOI: 10.1021/ol4005917

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


  52 in total

1.  Supported diazonium salts--convenient reagents for the combinatorial synthesis of azo dye.

Authors:  James Merrington; Mark James; Mark Bradley
Journal:  Chem Commun (Camb)       Date:  2002-01-21       Impact factor: 6.222

2.  Synthesis and photochemical properties of oligo-ortho-azobenzenes.

Authors:  Silvia Bellotto; Raphael Reuter; Christian Heinis; Hermann A Wegner
Journal:  J Org Chem       Date:  2011-11-01       Impact factor: 4.354

3.  A photocontrolled beta-hairpin peptide.

Authors:  Shou-Liang Dong; Markus Löweneck; Tobias E Schrader; Wolfgang J Schreier; Wolfgang Zinth; Luis Moroder; Christian Renner
Journal:  Chemistry       Date:  2006-01-23       Impact factor: 5.236

Review 4.  Heterocyclic azo dyestuffs in analytical chemistry. A review.

Authors:  R G Anderson; G Nickless
Journal:  Analyst       Date:  1967-04       Impact factor: 4.616

5.  New color chemosensors for monosaccharides based on azo dyes.

Authors:  N DiCesare; J R Lakowicz
Journal:  Org Lett       Date:  2001-11-29       Impact factor: 6.005

6.  Synthesis of Aryl Nitroso Derivatives by tert-Butyl Hypochlorite Oxidation in Homogeneous Media. Intermediates for the Preparation of High-Hyperpolarizability Chromophore Skeletons.

Authors:  M. H. Davey; V. Y. Lee; R. D. Miller; T. J. Marks
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

Review 7.  Synthesis of azobenzenes: the coloured pieces of molecular materials.

Authors:  Estíbaliz Merino
Journal:  Chem Soc Rev       Date:  2011-03-16       Impact factor: 54.564

8.  Gold-catalyzed synthesis of aromatic azo compounds from anilines and nitroaromatics.

Authors:  Abdessamad Grirrane; Avelino Corma; Hermenegildo García
Journal:  Science       Date:  2008-12-12       Impact factor: 47.728

9.  Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors:  Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  J Am Chem Soc       Date:  2008-06-13       Impact factor: 15.419

10.  From azides to nitrogen-centered radicals: applications of azide radical chemistry to organic synthesis.

Authors:  Matteo Minozzi; Daniele Nanni; Piero Spagnolo
Journal:  Chemistry       Date:  2009-08-10       Impact factor: 5.236

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  12 in total

1.  Cu-Catalyzed Aerobic Oxidative N-N Coupling of Carbazoles and Diarylamines Including Selective Cross-Coupling.

Authors:  Michael C Ryan; Joseph R Martinelli; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2018-07-16       Impact factor: 15.419

2.  Microwave-assisted rapid and sustainable synthesis of unsymmetrical azo dyes by coupling of nitroarenes with aniline derivatives.

Authors:  Ankit Thakuri; Mainak Banerjee; Amrita Chatterjee
Journal:  iScience       Date:  2022-05-31

3.  A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Org Biomol Chem       Date:  2013-11-21       Impact factor: 3.876

4.  Copper-catalyzed oxidative homo- and cross-coupling of Grignard reagents using diaziridinone.

Authors:  Yingguang Zhu; Tao Xiong; Wenyong Han; Yian Shi
Journal:  Org Lett       Date:  2014-11-24       Impact factor: 6.005

5.  Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer-Mills reactions.

Authors:  Miriam Schehr; Daniel Hugenbusch; Tobias Moje; Christian Näther; Rainer Herges
Journal:  Beilstein J Org Chem       Date:  2018-11-07       Impact factor: 2.883

6.  Direct Oxidative Azo Coupling of Anilines Using a Self-Assembled Flower-like CuCo2O4 Material as a Catalyst under Aerobic Conditions.

Authors:  Ashok Raj Patel; Geetika Patel; Gurupada Maity; Shiv P Patel; Sumantra Bhattacharya; Anjaneyulu Putta; Subhash Banerjee
Journal:  ACS Omega       Date:  2020-11-17

7.  Azo synthesis meets molecular iodine catalysis.

Authors:  Rozhin Rowshanpour; Travis Dudding
Journal:  RSC Adv       Date:  2021-02-11       Impact factor: 3.361

8.  Novel and Sustainable Colorants Developed via Incorporating Azo Chromophores into Dopamine Molecules.

Authors:  Suju Fan; Yintung Lam; Liang He; John H Xin
Journal:  ACS Omega       Date:  2022-03-23

9.  Visible Light-Emitting Diode Light-Driven Cu0.9Fe0.1@RCAC-Catalyzed Highly Selective Aerobic Oxidation of Alcohols and Oxidative Azo-Coupling of Anilines: Tandem One Pot Oxidation-Condensation to Imidazoles and Imines.

Authors:  Ashok Raj Patel; Geetika Patel; Subhash Banerjee
Journal:  ACS Omega       Date:  2019-12-19

10.  Oxidative Dehydrogenation of Hydrazobenzenes toward Azo Compounds Catalyzed by tert-Butyl Nitrite in EtOH.

Authors:  Zhi-Qiang Wang; Jiang-Xi Yu; Shan-Qin Bai; Bang Liu; Cheng-Yong Wang; Jin-Heng Li
Journal:  ACS Omega       Date:  2020-10-29
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