Literature DB >> 24353090

Rhodium(III)-catalyzed ortho alkenylation of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through C-H activation.

Fangdong Hu1, Ying Xia, Fei Ye, Zhenxing Liu, Chen Ma, Yan Zhang, Jianbo Wang.   

Abstract

A coupling reaction of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through Rh(III) -catalyzed CH activation is reported. In this reaction, ortho-alkenyl phenols were obtained in good yields and with excellent regio- and stereoselectivity. Rh-carbene migratory insertion is proposed as the key step in the reaction mechanism.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; diazo compounds; homogeneous catalysis; metal-carbene complexes; migratory insertion

Year:  2013        PMID： 24353090     DOI： 10.1002/anie.201309650

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

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Journal:  J Mol Model       Date:  2014-11-18       Impact factor: 1.810

2.  Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-09-11       Impact factor: 15.336

3.  Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.

Authors:  Hanbin Lee; Manoj V Mane; Ho Ryu; Debashis Sahu; Mu-Hyun Baik; Chae S Yi
Journal:  J Am Chem Soc       Date:  2018-08-03       Impact factor: 15.419

4.  Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

Authors:  Dianmin Zhang; Xiaofang He; Tao Yang; Song Liu
Journal:  ChemistryOpen       Date:  2022-02-24       Impact factor: 2.630

5.  A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis.

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Journal:  Nat Commun       Date:  2017-06-19       Impact factor: 14.919

6.  Unified synthesis of mono/bis-arylated phenols via RhIII-catalyzed dehydrogenative coupling.

Authors:  Qian Wu; Ying Chen; Dingyuan Yan; Muyue Zhang; Yi Lu; Wei-Yin Sun; Jing Zhao
Journal:  Chem Sci       Date:  2016-08-03       Impact factor: 9.825

7.  Catalytic Synthesis of Indolines by Hydrogen Atom Transfer to Cobalt(III)-Carbene Radicals.

Authors:  Alexander S Karns; Monalisa Goswami; Bas de Bruin
Journal:  Chemistry       Date:  2017-12-05       Impact factor: 5.236

8.  [2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines.

Authors:  Liang Ma; Feng Jin; Xionglve Cheng; Suyan Tao; Gangzhong Jiang; Xingxing Li; Jinwei Yang; Xiaoguang Bao; Xiaobing Wan
Journal:  Chem Sci       Date:  2021-06-22       Impact factor: 9.825

9.  Rh(III)-catalyzed cyclopropanation initiated by C-H activation: ligand development enables a diastereoselective [2 + 1] annulation of N-enoxyphthalimides and alkenes.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-08-05       Impact factor: 15.419

10.  Catalytic Dibenzocyclooctene Synthesis via Cobalt(III)-Carbene Radical and ortho-Quinodimethane Intermediates.

Authors:  Colet Te Grotenhuis; Naudin van den Heuvel; Jarl Ivar van der Vlugt; Bas de Bruin
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-06       Impact factor: 15.336
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