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“Anti-Michael addition” of Grignard reagents to sulfonylacetylenes: synthesis of alkynes

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Abstract

In this work, the addition of Grignard reagents to arylsulfonylacetylenes, which undergoes an “anti-Michael addition”, resulting in their alkynylation under very mild conditions is described. The simplicity of the experimental procedure and the functional group tolerance are the main features of this methodology. This is an important advantage over the use of organolithium at −78 °C that we previously reported. Moreover, the synthesis of diynes and other examples showing functional group tolerance in this anti-Michael reaction is also presented.

Graphical abstract: “Anti-Michael addition” of Grignard reagents to sulfonylacetylenes: synthesis of alkynes

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Publication details

The article was received on 29 Mar 2017, accepted on 06 Apr 2017 and first published on 06 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00783C
Citation: Org. Biomol. Chem., 2017, Advance Article
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    “Anti-Michael addition” of Grignard reagents to sulfonylacetylenes: synthesis of alkynes

    F. Esteban, L. Boughani, J. L. García Ruano, A. Fraile and J. Alemán, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00783C

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