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Gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: a combined experimental and computational study

Abstract

The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubsituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-subsituted o-(alkynyl)styrenes and a variety of alcohols as well as selected electron-rich aromatics, is reported. DFT calculations support the stereochemical outcome of the process that involves the formation of a key cyclopropyl gold carbene intermediate through a regiospecific 5-endo cyclization.

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Publication details

The article was received on 01 Oct 2019, accepted on 04 Nov 2019 and first published on 04 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02126D
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: a combined experimental and computational study

    C. Virumbrales, M. Solas, S. Suárez-Pantiga, M. A. Fernández-González, M. Marín Luna, C. S. Lopez and R. Sanz, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02126D

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