Experimental study reveals dual decarboxylation pathways in room-temperature Heck couplings of arene carboxylic acids, suggesting broad utility for mild peptide modification.
We report herein a Pd(II)-catalyzed Heck-type coupling between arene carboxylic acids and alkenes at room temperature. Mechanistically, the reaction proceeds in two distinct pathways where electron-rich substrates undergo a palladium(II)-catalyzed decarboxylation and electron-deficient substrates proceed through silver(I)-assisted decarboxylation. Dimethyl sulfoxide (DMSO) or sulfide ligands have positive and negative roles in the reaction outcome, respectively. The present protocol is combined for the peptide modification under mild reaction conditions.
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Hossian et al. (2016) studied this question.
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