Synthesis of Barbaralones and Bullvalenes Made Easy by Gold Catalysis

Sofia Ferrer; Antonio M Echavarren

doi:10.1002/anie.201606101

Synthesis of Barbaralones and Bullvalenes Made Easy by Gold Catalysis

Angew Chem Int Ed Engl. 2016 Sep 5;55(37):11178-82. doi: 10.1002/anie.201606101. Epub 2016 Aug 19.

Authors

Sofia Ferrer¹, Antonio M Echavarren^{2

3}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
² Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain. aechavarren@iciq.es.
³ Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007, Tarragona, Spain. aechavarren@iciq.es.

Abstract

The gold(I)-catalyzed oxidative cyclization of 7-ethynyl-1,3,5-cycloheptatrienes gives 1-substituted barbaralones in a general manner, which simplifies the access to other fluxional molecules. As an example, we report the shortest syntheses of bullvalene, phenylbullvalene, and disubstituted bullvalenes, and a readily accessible route to complex cage-type structures by further gold(I)-catalyzed reactions.

Keywords: barbaralones; bullvalenes; cyclization reactions; gold; valence tautomerism.

Publication types

Research Support, Non-U.S. Gov't