Rhodium-catalysed ortho-alkynylation of nitroarenes

Identifier:  imarina:9231661

Handle: https://hdl.handle.net/20.500.11797/imarina9231661

Authors:  Tan, Eric; Montesinos-Magraner, Marc; Garcia-Morales, Cristina; Mayans, Joan Guillem; Echavarren, Antonio M

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.