Literature DB >> 18327944

Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction.

Paul Ha-Yeon Cheong1, Philip Morganelli, Michael R Luzung, K N Houk, F Dean Toste.   

Abstract

Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.

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Year:  2008        PMID： 18327944      PMCID： PMC2995695          DOI： 10.1021/ja711058f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  38 in total

1.  The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes.

Authors:  Cristina Nieto-Oberhuber; Salomé López; Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chemistry       Date:  2006-08-07       Impact factor: 5.236

2.  Molecular diversity through gold catalysis with alkynes.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2006-11-09       Impact factor: 6.222

3.  Gold-catalyzed organic reactions.

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

4.  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

5.  Effect on kinetics by deuterium in the 1,5-hydrogen shift of a cisoid-locked 1,3(Z)-pentadiene, 2-methyl-10-methylenebicyclo[4.4.0]dec-1-ene: evidence for tunneling?

Authors:  William von E Doering; Xin Zhao
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

6.  Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates.

Authors:  Fahmi Himo; Timothy Lovell; Robert Hilgraf; Vsevolod V Rostovtsev; Louis Noodleman; K Barry Sharpless; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

7.  Regiospecific synthesis of bicyclo- and heterobicyclo-gem-difluorocyclobutenes using functionalized fluoroallenes and a novel Mo-catalyzed intramolecular [2 + 2] cycloaddition reaction.

Authors:  Qilong Shen; Gerald B Hammond
Journal:  J Am Chem Soc       Date:  2002-06-12       Impact factor: 15.419

8.  A DFT-based theoretical investigation of the mechanism of the PtCl2-mediated cycloisomerization of allenynes.

Authors:  Elena Soriano; José Marco-Contelles
Journal:  Chemistry       Date:  2005-01-07       Impact factor: 5.236

9.  Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes.

Authors:  Riadh Zriba; Vincent Gandon; Corinne Aubert; Louis Fensterbank; Max Malacria
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  PtCl 2-catalyzed cycloisomerizations of allenynes.

Authors:  Nicolas Cadran; Kevin Cariou; Gwénaëlle Hervé; Corinne Aubert; Louis Fensterbank; Max Malacria; José Marco-Contelles
Journal:  J Am Chem Soc       Date:  2004-03-24       Impact factor: 15.419
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  15 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.  Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

Authors:  Timothy J Brown; Dieter Weber; Michel R Gagné; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

3.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

4.  Mechanism of gold(I)-catalyzed rearrangements of acetylenic amine-N-oxides: computational investigations lead to a new mechanism confirmed by experiment.

Authors:  Elizabeth L Noey; Yingdong Luo; Liming Zhang; K N Houk
Journal:  J Am Chem Soc       Date:  2011-12-22       Impact factor: 15.419

5.  Experimental and computational evidence for gold vinylidenes: generation from terminal alkynes via a bifurcation pathway and facile C-H insertions.

Authors:  Longwu Ye; Yanzhao Wang; Donald H Aue; Liming Zhang
Journal:  J Am Chem Soc       Date:  2011-12-28       Impact factor: 15.419

6.  Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

Authors:  Pablo Mauleón; Jamin L Krinsky; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

7.  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

8.  Dissecting Anion Effects in Gold(I)-Catalyzed Intermolecular Cycloadditions.

Authors:  Anna Homs; Carla Obradors; David Lebœuf; Antonio M Echavarren
Journal:  Adv Synth Catal       Date:  2014-01-13       Impact factor: 5.837

9.  Intriguing mechanistic labyrinths in gold(I) catalysis.

Authors:  Carla Obradors; Antonio M Echavarren
Journal:  Chem Commun (Camb)       Date:  2014-01-04       Impact factor: 6.222

10.  Anatomy of gold catalysts: facts and myths.

Authors:  Beatrice Ranieri; Imma Escofet; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2015-06-09       Impact factor: 3.876
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