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Molecules 2018, 23(8), 2051; https://doi.org/10.3390/molecules23082051

Suzuki-Type Cross-Coupling Reaction of Unprotected 3-Iodoindazoles with Pinacol Vinyl Boronate: An Expeditive C-3 Vinylation of Indazoles under Microwave Irradiation

1
Departamento de Farmacia, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Avda. Vicuña Mackenna 4860, Macul 7820436, Santiago, Chile
2
Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Avda. Vicuña Mackenna 4860, Macul 7820436, Santiago, Chile
3
Centro Interdisciplinario de Neurociencias, Pontificia Universidad Católica de Chile, Marcoleta 391, Santiago 8330024, Santiago, Chile
*
Author to whom correspondence should be addressed.
Received: 7 July 2018 / Revised: 11 August 2018 / Accepted: 14 August 2018 / Published: 16 August 2018
(This article belongs to the Special Issue Recent Advances in Nitrogen-Containing Aromatic Heterocycles)
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Abstract

Herein we report an expeditive C-3 vinylation of unprotected 3-iodoindazoles under microwave irradiation. Ten C-5 substituted 3-vinylindazole derivatives, nine of them novel, were synthesized through this method, which proceeds in moderate to excellent yields starting from C-5 substituted 3-iodoindazole derivatives. In all cases, the C-3 vinylated derivative was the only isolated product. This methodology allows access to 3-vinylated indazoles selectively and directly without the need of N-protection. 3-Vinylindazoles could be interesting synthetic intermediates allowing access to biologically active molecules. View Full-Text
Keywords: vinylation; Suzuki cross-coupling; 3-iodoindazole; 3-vinylindazole; microwave synthesis vinylation; Suzuki cross-coupling; 3-iodoindazole; 3-vinylindazole; microwave synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Vera, G.; Diethelm, B.; Terraza, C.A.; Recabarren-Gajardo, G. Suzuki-Type Cross-Coupling Reaction of Unprotected 3-Iodoindazoles with Pinacol Vinyl Boronate: An Expeditive C-3 Vinylation of Indazoles under Microwave Irradiation. Molecules 2018, 23, 2051.

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