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Issue 40, 2018
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Gold(i)-catalysed high-yielding synthesis of indenes by direct Csp3–H bond activation

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Abstract

A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct Csp3–H activation under gold(I) catalysis was developed. The scope of the protocol was determined by synthesizing some electron-neutral, electron-poor as well as electron-rich derivatives including the dibenzofurane and carbazole heterocycles. The mechanism of this reaction was elucidated by theoretical calculations using a ONIOM(M08-HX/mixed-basis:PM6) hybrid scheme. Thereby we found a pericyclic transformation involving a [1,5]-H shift generating a gold(I)–carbene that evolves to the indene derivative. In comparison with several reports, our protocol presents a direct activation of the Csp3–H bond.

Graphical abstract: Gold(i)-catalysed high-yielding synthesis of indenes by direct Csp3–H bond activation

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Supplementary files

Article information


Submitted
22 Aug 2018
Accepted
21 Sep 2018
First published
21 Sep 2018

Org. Biomol. Chem., 2018,16, 7330-7335
Article type
Communication

Gold(I)-catalysed high-yielding synthesis of indenes by direct Csp3–H bond activation

P. D. Nahide, J. O. C. Jiménez-Halla, K. Wrobel, C. R. Solorio-Alvarado, R. Ortiz Alvarado and B. Yahuaca-Juárez, Org. Biomol. Chem., 2018, 16, 7330
DOI: 10.1039/C8OB02056F

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