Experimental and computational studies on the mechanism of the Pd-catalyzed C(sp3)–H γ-arylation of amino acid derivatives assisted by the 2-pyridylsulfonyl group

doi:10.1039/C4SC00848K

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Experimental and computational studies on the mechanism of the Pd-catalyzed C(sp3)–H γ-arylation of amino acid derivatives assisted by the 2-pyridylsulfonyl group

Published Aug 26, 2014 · A. Poveda, I. Alonso, M. Fernández‐Ibáñez

Chemical Science

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Abstract

The Pd(OAc)2-catalyzed γ-arylation of amino acid esters bearing a removable N-(2-pyridyl)sulfonyl directing group via C(sp3)–H activation provides a direct method to form functionalized amino acids without racemization at the α-C and with a high degree of stereoselectivity. The present mechanistic studies suggest that the reaction proceeds via a catalytically active monomeric species, and that the C–H activation is reversible and is not always the turnover limiting step. Moreover, theoretical calculations explain the observed stereoselectivity and suggest that the reaction proceeds through a Pd(II)/Pd(IV) mechanism.

Study Snapshot

The Pd(OAc)2-catalyzed -arylation of amino acid esters with removable N-(2-pyridyl)sulfonyl directing group allows for functionalized amino acids with high stereoselectivity and reversible C-H activation.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Experimental and computational studies on the mechanism of the Pd-catalyzed C(sp3)–H γ-arylation of amino acid derivatives assisted by the 2-pyridylsulfonyl group

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