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Updated: Oct 12, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Rhodium-catalysed ortho-alkynylation of nitroarenes
Eric Tan1,2, Marc Montesinos-Magraner1, Cristina García-Morales1,2
1Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST) Av. Països Catalans 16 43007 Tarragona Spain aechavarren@iciq.es.
Abstract:
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.
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