Literature DB >> 23788447

Gold-catalyzed cyclizations of cis-enediynes: insights into the nature of gold-aryne interactions.

Youliang Wang1, Akop Yepremyan, Subir Ghorai, Robert Todd, Donald H Aue, Liming Zhang.   

Abstract

Golden aryne? Gold aryne complexes are inferred as transition states in dual gold-catalyzed cyclizations of cis-enediynes (see scheme; DCE = 1,2-dichloroethane). They are better described as ortho-aurophenyl cations, which react with weak nucleophiles and undergo facile intramolecular insertions into C(sp(3))-H bonds. Indanes, fused heteroarenes, and phenol derivatives are readily prepared using this method.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH insertion; arynes; gold; heterocycles; homogeneous catalysis

Mesh：

Substances：

Year:  2013        PMID： 23788447      PMCID： PMC4120750          DOI： 10.1002/anie.201301057

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


  34 in total

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3.  Arynes and cyclohexyne in natural product synthesis.

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4.  Dinuclear gold catalysis: are two gold centers better than one?

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

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Authors:  Longwu Ye; Weimin He; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

7.  Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways.

Authors:  A Stephen K Hashmi; Marcel Wieteck; Ingo Braun; Matthias Rudolph; Frank Rominger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336

8.  Zirconocene complexes of unsaturated organic molecules: new vehicles for organic synthesis.

Authors:  R D Broene; S L Buchwald
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9.  Mechanistic switch in dual gold catalysis of diynes: C(sp(3))-H activation through bifurcation--vinylidene versus carbene pathways.

Authors:  Max M Hansmann; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-30       Impact factor: 15.336

10.  Gold(I)-catalyzed regioselective inter-/intramolecular addition cascade of di- and triynes for direct construction of substituted naphthalenes.

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Journal:  J Org Chem       Date:  2012-05-15       Impact factor: 4.354
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  4 in total

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Authors:  Stephanie R Hare; Dean J Tantillo
Journal:  Chem Sci       Date:  2016-10-21       Impact factor: 9.825

3.  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

4.  A Switchable Gold Catalyst by Encapsulation in a Self-Assembled Cage.

Authors:  Anne C H Jans; Adrián Gómez-Suárez; Steven P Nolan; Joost N H Reek
Journal:  Chemistry       Date:  2016-09-04       Impact factor: 5.236
  4 in total

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