Literature DB >> 20589279

Domino gold-catalyzed rearrangement and fluorination of propargyl acetates.

Teresa de Haro1, Cristina Nevado.   

Abstract

A combination of IPrAuNTf(2) as catalyst in the presence of Selectfluor has been successfully used for the high yielding synthesis of α-fluoroenones via 1,3-acyloxy rearrangement of propargyl acetates followed by Csp(2)-F bond formation, likely involving a redox Au(I)/Au(III) catalytic cycle.

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Year:  2010        PMID: 20589279     DOI: 10.1039/c002679d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  7 in total

Review 1.  Bystanding F+ oxidants enable selective reductive elimination from high-valent metal centers in catalysis.

Authors:  Keary M Engle; Tian-Sheng Mei; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-24       Impact factor: 15.336

2.  Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles.

Authors:  Antoine Simonneau; Pierre Garcia; Jean-Philippe Goddard; Virginie Mouriès-Mansuy; Max Malacria; Louis Fensterbank
Journal:  Beilstein J Org Chem       Date:  2011-10-07       Impact factor: 2.883

Review 3.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

4.  Aminofluorination of 2-alkynylanilines: a Au-catalyzed entry to fluorinated indoles.

Authors:  Antonio Arcadi; Emanuela Pietropaolo; Antonello Alvino; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2014-02-20       Impact factor: 2.883

5.  Regioselective dihalohydration reactions of propargylic alcohols: gold-catalyzed and noncatalyzed reactions.

Authors:  Jarryl M D'Oyley; Abil E Aliev; Tom D Sheppard
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-21       Impact factor: 15.336

6.  Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols.

Authors:  Matthew N Pennell; Michael P Kyle; Samantha M Gibson; Louise Male; Peter G Turner; Richard S Grainger; Tom D Sheppard
Journal:  Adv Synth Catal       Date:  2016-04-27       Impact factor: 5.837

Review 7.  Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones.

Authors:  Pakorn Bovonsombat; Punyanuch Sophanpanichkul; Satreerat Losuwanakul
Journal:  RSC Adv       Date:  2022-08-12       Impact factor: 4.036

  7 in total

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