Rhodium-catalysed ortho-alkynylation of nitroarenes

Chem Sci. 2021 Oct 11;12(44):14731-14739. doi: 10.1039/d1sc04527j. eCollection 2021 Nov 17.

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.

PMID:34820088 | PMC:PMC8597868 | DOI:10.1039/d1sc04527j

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