Literature DB >> 21512612

Gold(I)-catalyzed intermolecular hydroarylation of allenes with nucleophilic arenes: scope and limitations.

Michael A Tarselli1, Ann Liu, Michel R Gagné.   

Abstract

The addition of nucleophilic methoxyarenes to allenes proceeds at room temperature in dichloromethane with a catalytic amount of phosphite-gold(I) precatalyst and silver additive. The addition is regioselective for the allene terminus, and generates E-allylation products without the need for prefunctionalization of the synthons as organometallics or allyl bromides. Coordinating heteroaromatics and sterically hindered allenes do not participate in the reaction.

Entities:  

Year:  2009        PMID： 21512612      PMCID： PMC3079221          DOI： 10.1016/j.tet.2008.10.110

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  15 in total

1.  Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer.

Authors:  Naoko Nishina; Yoshinori Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-12       Impact factor: 15.336

Review 2.  Relativistic effects in homogeneous gold catalysis.

Authors:  David J Gorin; F Dean Toste
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

3.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

4.  Recent developments in enantioselective gold(I) catalysis.

Authors:  Ross A Widenhoefer
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

5.  Phosphine gold(I) bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes.

Authors:  Nicolas Mézailles; Louis Ricard; Fabien Gagosz
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

6.  Chloroprene as a source of fine chemicals: palladium-catalyzed synthesis of terminal allenes.

Authors:  M Ogasawara; H Ikeda; T Nagano; T Hayashi
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

7.  Gold(I)-catalyzed intermolecular cyclopropanation of enynes with alkenes: trapping of two different gold carbenes.

Authors:  Salomé López; Elena Herrero-Gómez; Patricia Pérez-Galán; Cristina Nieto-Oberhuber; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

8.  Gold-catalyzed hydroarylation of allenes: a highly regioselective carbon-carbon bond formation producing six-membered rings.

Authors:  Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno
Journal:  Org Lett       Date:  2007-10-09       Impact factor: 6.005

9.  Regio- and stereoselective synthesis of alkyl allylic ethers via gold(I)-catalyzed intermolecular hydroalkoxylation of allenes with alcohols.

Authors:  Zhibin Zhang; Ross A Widenhoefer
Journal:  Org Lett       Date:  2008-04-16       Impact factor: 6.005

10.  Efficient functionalization of aromatic C-H bonds catalyzed by gold(III) under mild and solvent-free conditions.

Authors:  Zhangjie Shi; Chuan He
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354
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  8 in total

1.  Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors:  Dieter Weber; Michael A Tarselli; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

3.  Gold(I)-Catalyzed Hydroarylation of Allenes with Indoles.

Authors:  Kristina L Toups; Gordon T Liu; Ross A Widenhoefer
Journal:  J Organomet Chem       Date:  2009-02-15       Impact factor: 2.369

4.  Gold(I)-catalyzed cascade cyclization of allenyl epoxides.

Authors:  Michael A Tarselli; J Lucas Zuccarello; Stephen J Lee; Michel R Gagné
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

5.  Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Authors:  Cong Liu; Ross A Widenhoefer
Journal:  Org Lett       Date:  2007-04-12       Impact factor: 6.005

6.  Recent advances in the gold-catalyzed additions to C-C multiple bonds.

Authors:  He Huang; Yu Zhou; Hong Liu
Journal:  Beilstein J Org Chem       Date:  2011-07-04       Impact factor: 2.883

7.  Metal-free hydroarylation of the side chain carbon-carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid.

Authors:  Anna S Zalivatskaya; Dmitry S Ryabukhin; Marina V Tarasenko; Alexander Yu Ivanov; Irina A Boyarskaya; Elena V Grinenko; Ludmila V Osetrova; Eugeniy R Kofanov; Aleksander V Vasilyev
Journal:  Beilstein J Org Chem       Date:  2017-05-11       Impact factor: 2.883

8.  Synthesis of a Novel Type of 2,3'-BIMs via Platinum-Catalysed Reaction of Indolylallenes with Indoles.

Authors:  Lisa Cooper; José Miguel Alonso; Louise Eagling; Helen Newson; Sachini Herath; Christopher Thomson; Andrew Lister; Catherine Howsham; Brian Cox; María Paz Muñoz
Journal:  Chemistry       Date:  2018-03-05       Impact factor: 5.236
  8 in total

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