Literature DB >> 18278940

Gold(I)-catalyzed intramolecular hydroarylation of allenes.

Michael A Tarselli1, Michel R Gagné.   

Abstract

Gold(I) complexes react with 4-allenyl arenes in an exo fashion to furnish vinyl-substituted benzocycles. Phosphite gold(I) monocations were found to be optimal, and the catalyst was tolerant of ethers, esters, and pyrroles. Reactions proceeded in unpurified solvent at room temperature.

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Year:  2008        PMID： 18278940      PMCID： PMC2924810          DOI： 10.1021/jo7024948

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


  18 in total

1.  A New Gold-Catalyzed C-C Bond Formation This work was supported by the Deutsche Forschungsgemeinschaft (Ha 1932/5-1, Ha 1932/6-1) and the Fonds der Chemischen Industrie. Gold salts were donated by Degussa-Hüls AG. A.S.K.H. is indebted to Prof. M. Göbel for laboratory space.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-07-03       Impact factor: 15.336

2.  Gold-catalyzed organic reactions.

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

3.  Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors:  Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-09-21       Impact factor: 15.419

4.  Gold(I)-catalyzed asymmetric cycloisomerization of eneallenes into vinylcyclohexenes.

Authors:  Michael A Tarselli; Anthony R Chianese; Stephen J Lee; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Au(I)-catalyzed annulation of enantioenriched allenes in the enantioselective total synthesis of (-)-rhazinilam.

Authors:  Zuosheng Liu; Andrew S Wasmuth; Scott G Nelson
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

6.  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

7.  AuCl-catalyzed synthesis of benzyl-protected substituted phenols: a formal [3+3] approach.

Authors:  Xiaogen Huang; Liming Zhang
Journal:  Org Lett       Date:  2007-10-03       Impact factor: 6.005

8.  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

9.  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

10.  Remarkably mild and efficient intramolecular Friedel-Crafts cyclization catalyzed by In(III).

Authors:  Ryuji Hayashi; Gregory R Cook
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005
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  11 in total

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

Authors:  Michael A Tarselli; Ann Liu; Michel R Gagné
Journal:  Tetrahedron       Date:  2009-02       Impact factor: 2.457

2.  Synthesis of flinderoles B and C by a gold-catalyzed allene hydroarylation().

Authors:  Rachel M Zeldin; F Dean Toste
Journal:  Chem Sci       Date:  2011-06-24       Impact factor: 9.825

3.  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

4.  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

5.  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

6.  Dinuclear gold-silver resting states may explain silver effects in gold(I)-catalysis.

Authors:  Dieter Weber; Michel R Gagné
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

7.  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

8.  Platinum(II) Enyne Cycloisomerization Catalysis: Intermediates and Resting States.

Authors:  D Luke Nelsen; Michel R Gagné
Journal:  Organometallics       Date:  2009-02-23       Impact factor: 3.876

9.  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

10.  Rhodium-catalyzed asymmetric intramolecular hydroarylation of allenes: access to functionalized benzocycles.

Authors:  Dino Berthold; Johannes Klett; Bernhard Breit
Journal:  Chem Sci       Date:  2019-09-10       Impact factor: 9.825
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