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Issue 46, 2019
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Gold(i)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: a combined experimental and computational study

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Abstract

The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-substituted 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.

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

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Article information


Submitted
01 Oct 2019
Accepted
04 Nov 2019
First published
04 Nov 2019

Org. Biomol. Chem., 2019,17, 9924-9932
Article type
Paper

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-Rodríguez, M. Marín-Luna, C. S. López and R. Sanz, Org. Biomol. Chem., 2019, 17, 9924
DOI: 10.1039/C9OB02126D

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