Literature DB >> 24338996

Dehydrogenative Meyer-Schuster-like rearrangement: a gold-catalyzed reaction generating an alkyne.

Yang Yu1, Weibo Yang, Daniel Pflästerer, A Stephen K Hashmi.   

Abstract

Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz's catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer-Schuster rearrangement.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; allenes; esters; gold; hypervalent iodine

Year:  2013        PMID： 24338996     DOI： 10.1002/anie.201307647

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


  7 in total

1.  Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.

Authors:  Jin Wang; Chiyu Wei; Xuming Li; Pengyi Zhao; Chuan Shan; Lukasz Wojtas; Hao Chen; Xiaodong Shi
Journal:  Chemistry       Date:  2020-04-14       Impact factor: 5.236

2.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

Review 3.  Metal-Catalyzed Haloalkynylation Reactions.

Authors:  Mathis Kreuzahler; Gebhard Haberhauer
Journal:  Chemistry       Date:  2021-11-18       Impact factor: 5.020

4.  Stereo- and Regioselective Alkyne Hydrometallation with Gold(III) Hydrides.

Authors:  Anna Pintus; Luca Rocchigiani; Julio Fernandez-Cestau; Peter H M Budzelaar; Manfred Bochmann
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-04       Impact factor: 15.336

5.  Highly Regioselective Synthesis of Oxindolyl-Pyrroles and Quinolines via a One-Pot, Sequential Meyer-Schuster Rearrangement, Anti-Michael Addition/C(sp3)-H Functionalization, and Azacyclization.

Authors:  Srinivasarao Yaragorla; Ravikrishna Dada; P Rajesh; Manju Sharma
Journal:  ACS Omega       Date:  2018-03-09

6.  Gold-catalyzed 1,3-transposition of ynones.

Authors:  Roohollah Kazem Shiroodi; Mohammad Soltani; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-07-02       Impact factor: 15.419

7.  Cyclopropenylmethyl Cation: A Concealed Intermediate in Gold(I)-Catalyzed Reactions.

Authors:  Mathis Kreuzahler; Gebhard Haberhauer
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-10       Impact factor: 16.823
  7 in total

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