Organocatalytic decarboxylative alkylation of N-hydroxy-phthalimide esters enabled by pyridine-boryl radicals?

Chemical Communications Pub Date: 2018-09-04 DOI: 10.1039/C8CC06152A

Abstract

The decarboxylative alkylation of N-hydroxyphthalimide (NHPI) based reactive esters with olefins has been achieved via an organocatalytic strategy. Control experiments and density functional theory calculations suggest that these reactions involve a boryl-radical mediated decarboxylation pathway, which is different from the single electron transfer involved in decarboxylative alkylation reactions reported previously. This metal-free decarboxylative alkylation reaction features good functional compatibility, and broad substrate scope illustrated by the transformations of both the alkyl and aryl carboxylic acid derivatives.

Graphical abstract: Organocatalytic decarboxylative alkylation of N-hydroxy-phthalimide esters enabled by pyridine-boryl radicals
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