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 n class="Chemical">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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