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Rhodium-catalysed ortho-alkynylation of nitroarenes† † Electronic supplementary information (ESI) available: Supplemental figures, synthetic and computational details, spectra for synthesized compounds. See DOI: 10.1039/d1sc04527j

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.

SUBMITTER: Tan E

PROVIDER: S-EPMC8597868 | biostudies-literature |

REPOSITORIES: biostudies-literature

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