Literature DB >> 19848386

The Au(I)-catalyzed intramolecular hydroarylation of terminal alkynes under mild conditions: application to the synthesis of 2H-chromenes, coumarins, benzofurans, and dihydroquinolines.

Rajeev S Menon1, Alison D Findlay, Alex C Bissember, Martin G Banwell.   

Abstract

Operationally simple Au(I)-catalyzed intramolecular hydroarylation (IMHA) reactions of terminal alkynes that proceed in high yield and under very mild conditions are described. These processes involve low catalyst loadings, mild reaction temperatures, and short reaction times, require no cocatalysts or additives, and allow for the generation of a number of important heterocyclic motifs from readily accessible starting materials.

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Year:  2009        PMID: 19848386     DOI: 10.1021/jo902032p

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

1.  Mechanism of AuCl₃-catalyzed cyclization of 1-(indol-2-yl)-3-alkyn-1-ols: a DFT study.

Authors:  Jingna Shao; Rongxing He; Wei Shen; Ming Li
Journal:  J Mol Model       Date:  2014-05-07       Impact factor: 1.810

2.  Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers.

Authors:  Yanzhao Wang; Kegong Ji; Sylvester Lan; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-13       Impact factor: 15.336

3.  Au-Cavitands: Size governed arene-alkyne cycloisomerization.

Authors:  Lisa E Rusali; Michael P Schramm
Journal:  Tetrahedron Lett       Date:  2020-08-16       Impact factor: 2.415

4.  Discovery of cyclopropyl chromane-derived pyridopyrazine-1,6-dione γ-secretase modulators with robust central efficacy.

Authors:  Martin Pettersson; Douglas S Johnson; Danica A Rankic; Gregory W Kauffman; Christopher W Am Ende; Todd W Butler; Brian Boscoe; Edelweiss Evrard; Christopher J Helal; John M Humphrey; Antonia F Stepan; Cory M Stiff; Eddie Yang; Longfei Xie; Kelly R Bales; Eva Hajos-Korcsok; Stephen Jenkinson; Betty Pettersen; Leslie R Pustilnik; David S Ramirez; Stefanus J Steyn; Kathleen M Wood; Patrick R Verhoest
Journal:  Medchemcomm       Date:  2016-11-02       Impact factor: 3.597

5.  Syntheses of α-pyrones using gold-catalyzed coupling reactions.

Authors:  Tuoping Luo; Mingji Dai; Shao-Liang Zheng; Stuart L Schreiber
Journal:  Org Lett       Date:  2011-05-02       Impact factor: 6.005

6.  Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride.

Authors:  Sergio Pascual; Christophe Bour; Paula de Mendoza; Antonio M Echavarren
Journal:  Beilstein J Org Chem       Date:  2011-11-14       Impact factor: 2.883

7.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

8.  Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives.

Authors:  Pablo Morán-Poladura; Eduardo Rubio; José M González
Journal:  Beilstein J Org Chem       Date:  2013-10-16       Impact factor: 2.883

9.  High-affinity ligands of the colchicine domain in tubulin based on a structure-guided design.

Authors:  Oskía Bueno; Juan Estévez Gallego; Solange Martins; Andrea E Prota; Federico Gago; Asier Gómez-SanJuan; María-José Camarasa; Isabel Barasoain; Michel O Steinmetz; J Fernando Díaz; María-Jesús Pérez-Pérez; Sandra Liekens; Eva-María Priego
Journal:  Sci Rep       Date:  2018-03-09       Impact factor: 4.379

10.  Alkyne hydroarylation with Au N-heterocyclic carbene catalysts.

Authors:  Cristina Tubaro; Marco Baron; Andrea Biffis; Marino Basato
Journal:  Beilstein J Org Chem       Date:  2013-02-05       Impact factor: 2.883

  10 in total

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