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Issue 82, 2018
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Organocatalytic decarboxylative alkylation of N-hydroxy-phthalimide esters enabled by pyridine-boryl radicals

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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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Article information


Submitted
28 Jul 2018
Accepted
04 Sep 2018
First published
04 Sep 2018

Chem. Commun., 2018,54, 11534-11537
Article type
Communication

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

L. Gao, G. Wang, J. Cao, D. Yuan, C. Xu, X. Guo and S. Li, Chem. Commun., 2018, 54, 11534
DOI: 10.1039/C8CC06152A

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