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Issue 10, 2014
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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

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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.

Graphical abstract: 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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Article information


Submitted
21 Mar 2014
Accepted
28 May 2014
First published
02 Jun 2014

Chem. Sci., 2014,5, 3873-3882
Article type
Edge Article
Author version available

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

A. Poveda, I. Alonso and M. Á. Fernández-Ibáñez, Chem. Sci., 2014, 5, 3873
DOI: 10.1039/C4SC00848K

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