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Molecules 2017, 22(7), 1178; doi:10.3390/molecules22071178

Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles

Aix-Marseille University, CNRS, ICR UMR 7273, Equipe Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, 27 Boulevard Jean Moulin, CS 30064, 13385 Marseille CEDEX 05, France
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Received: 4 July 2017 / Accepted: 11 July 2017 / Published: 14 July 2017
(This article belongs to the Section Organic Synthesis)
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Abstract

A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity. View Full-Text
Keywords: metal-free; regiodivergent; α,β-unsaturated electrophiles metal-free; regiodivergent; α,β-unsaturated electrophiles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Spitz, C.; Giuglio-Tonolo, A.G.; Terme, T.; Vanelle, P. Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles. Molecules 2017, 22, 1178.

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