Issue 44, 2021

Rhodium-catalysed ortho-alkynylation of nitroarenes


The ortho-alkynylation of nitro-(hetero)arenes takes place in the presence of a Rh(III) catalyst to deliver a wide variety of alkynylated nitroarenes regioselectively. These interesting products could be further derivatized by selective reduction of the nitro group or palladium-catalysed couplings. Experimental and computational mechanistic studies demonstrate that the reaction proceeds via a turnover-limiting electrophilic C–H metalation ortho to the strongly electron-withdrawing nitro group.

Graphical abstract: Rhodium-catalysed ortho-alkynylation of nitroarenes

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Article information

Article type
Edge Article
16 Aug 2021
11 Oct 2021
First published
11 Oct 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 14731-14739

Rhodium-catalysed ortho-alkynylation of nitroarenes

E. Tan, M. Montesinos-Magraner, C. García-Morales, J. G. Mayans and A. M. Echavarren, Chem. Sci., 2021, 12, 14731 DOI: 10.1039/D1SC04527J

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