Literature DB >> 23865434

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes.

Akira Yoshimura1, Kyle R Middleton, Anthony D Todora, Brent J Kastern, Steven R Koski, Andrey V Maskaev, Viktor V Zhdankin.   

Abstract

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

Entities:  

Year:  2013        PMID： 23865434     DOI： 10.1021/ol401815n

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


  9 in total

1.  A theoretical study on diastereoselective oxidative dearomatization by iodoxybenzoic acid.

Authors:  Vincent Tognetti; Agathe Boulangé; Philippe A Peixoto; Xavier Franck; Laurent Joubert
Journal:  J Mol Model       Date:  2014-07-20       Impact factor: 1.810

2.  Mechanochemical Dimerization of Aldoximes to Furoxans.

Authors:  Run-Kai Fang; Kuan Chen; Chuang Niu; Guan-Wu Wang
Journal:  Molecules       Date:  2022-04-18       Impact factor: 4.927

Review 3.  Total synthesis of natural products using hypervalent iodine reagents.

Authors:  Gaëtan Maertens; Chloé L'Homme; Sylvain Canesi
Journal:  Front Chem       Date:  2015-01-05       Impact factor: 5.221

4.  Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al2O3 surface under ball-milling conditions.

Authors:  Rafael A Hernandez R; Kelly Burchell-Reyes; Arthur P C A Braga; Jennifer Keough Lopez; Pat Forgione
Journal:  RSC Adv       Date:  2022-02-23       Impact factor: 3.361

5.  Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes.

Authors:  Irina A Mironova; Valentine G Nenajdenko; Pavel S Postnikov; Akio Saito; Mekhman S Yusubov; Akira Yoshimura
Journal:  Molecules       Date:  2022-06-16       Impact factor: 4.927

6.  Electrochemical Synthesis of Isoxazolines: Method and Mechanism.

Authors:  Samuel D L Holman; Alfie G Wills; Neal J Fazakerley; Darren L Poole; Diane M Coe; Leonard A Berlouis; Marc Reid
Journal:  Chemistry       Date:  2022-02-10       Impact factor: 5.020

7.  [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

8.  Characterization and Engineering of the Adenylation Domain of a NRPS-Like Protein: A Potential Biocatalyst for Aldehyde Generation.

Authors:  Meng Wang; Huimin Zhao
Journal:  ACS Catal       Date:  2014-03-17       Impact factor: 13.084

Review 9.  Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds.

Authors:  Helen A Goulart; Daniela R Araujo; Filipe Penteado; Raquel G Jacob; Gelson Perin; Eder J Lenardão
Journal:  Molecules       Date:  2021-12-12       Impact factor: 4.411
  9 in total

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