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

Molecules

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.

Published: July 2017

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 to α,β-unsaturated aldehydes in the presence of TDAE. Moreover, the reaction between -nitrobenzyl chloride and α,β-unsaturated iminium salts led to the formation of the 1,4-adduct with total regioselectivity.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152382PMC
http://dx.doi.org/10.3390/molecules22071178DOI Listing

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