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Rhodium-catalysed ortho-alkynylation of nitroarenes |
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| Authors: | Eric Tan Marc Montesinos-Magraner Cristina García-Morales Joan Guillem Mayans Antonio M Echavarren |
| Institution: | Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology (BIST), Av. Països Catalans 16, 43007 Tarragona Spain.; Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel·lí Domingo s/n, 43007 Tarragona Spain |
| 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.Rh(iii)-catalyzed ortho-alkynylation of nitro-(hetero)arenes leads to a wide variety of alkynylated nitroarenes via a turnover-limiting electrophilic C–H ortho-metalation. |
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