Literature DB >> 20698529

Gold-catalyzed annulation/fragmentation: formation of free gold carbenes by retro-cyclopropanation.

César R Solorio-Alvarado1, Antonio M Echavarren.   

Abstract

The gold(I)-catalyzed cyclization of 1-(prop-2-yn-1-yl)-2-alkenylbenzenes substituted at the benzylic position with OR groups gives 1,3-disubstituted naphthalenes with concomitant fragmentation of the alkene. One of these annulations proceeds by a retro-cyclopropanation that leads to free gold(I) carbenes.

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Year:  2010        PMID： 20698529     DOI： 10.1021/ja104743k

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


  10 in total

1.  Gold(I) carbenes by retro-Buchner reaction: generation and fate.

Authors:  Yahui Wang; Paul R McGonigal; Bart Herlé; Maria Besora; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2013-12-31       Impact factor: 15.419

2.  Gold-catalyzed rearrangements and beyond.

Authors:  Carla Obradors; Antonio M Echavarren
Journal:  Acc Chem Res       Date:  2013-10-31       Impact factor: 22.384

3.  Gold(I)-catalyzed 6-endo hydroxycyclization of 7-substituted-1,6-enynes.

Authors:  Ana M Sanjuán; Alberto Martínez; Patricia García-García; Manuel A Fernández-Rodríguez; Roberto Sanz
Journal:  Beilstein J Org Chem       Date:  2013-10-29       Impact factor: 2.883

4.  Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.

Authors:  M Elena de Orbe; Laura Amenós; Mariia S Kirillova; Yahui Wang; Verónica López-Carrillo; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

5.  Stereoselective cis-Vinylcyclopropanation via a Gold(I)-Catalyzed Retro-Buchner Reaction under Mild Conditions.

Authors:  Bart Herlé; Philipp M Holstein; Antonio M Echavarren
Journal:  ACS Catal       Date:  2017-04-18       Impact factor: 13.084

6.  Gold(I)-Catalyzed Synthesis of Indenes and Cyclopentadienes: Access to (±)-Laurokamurene B and the Skeletons of the Cycloaurenones and Dysiherbols.

Authors:  Xiang Yin; Mauro Mato; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-11       Impact factor: 15.336

7.  Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects.

Authors:  Gen-Qiang Chen; Wei Fang; Yin Wei; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825

8.  Balancing Bulkiness in Gold(I) Phosphino-triazole Catalysis.

Authors:  Yiming Zhao; Matthew G Wakeling; Fernanda Meloni; Tze Jing Sum; Huy van Nguyen; Benjamin R Buckley; Paul W Davies; John S Fossey
Journal:  European J Org Chem       Date:  2019-07-30

9.  Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes.

Authors:  De-Yao Li; Yin Wei; Ilan Marek; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2015-06-24       Impact factor: 9.825

10.  Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, C-H Insertion, and Dimerization Reactions.

Authors:  Cristina García-Morales; Xiao-Li Pei; Juan M Sarria Toro; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-11       Impact factor: 15.336
  10 in total

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