Stereospecific Synthesis of 3,3-Disubstituted Acrylonitriles by Heck Reaction

Abstract

The coupling reaction of 3-aryl (or heteroaryl) acrylonitriles with several aryl and heteroaryl iodides (Heck reaction) under Jeffery's conditions has been studied as a concept to synthesize, in a stereospecific manner, trisubstituted olefins.

AlBr3-Promoted stereoselective anti-hydroarylation of the acetylene bond in 3-arylpropynenitriles by electron-rich arenes: synthesis of 3,3-diarylpropenenitriles

“…)-free stereoselective way for the synthesis of compounds 2 . These compounds can be alternatively obtained by a Pd-catalyzed Heck reaction of 3-arylpropenenitriles with iodoarenes [ 23 ] or by a Cu-catalyzed hydroarylation of 3-arylpropynenitriles with arylboronic acid [ 24 – 25 ]. There is one example of use of dicyanoacetylene in a similar AlCl 3 -catalyzed hydroarylation of an acetylene bond in the synthesis of cyclophanes [ 26 ].…”

Stereoselective synthesis of Z-acrylonitrile derivatives: catalytic and acetylcholinesterase inhibition studies

“…The synthesis of acrylonitrile compounds has previously been achieved by the use of Wittig reactions, 27 McMurry coupling reactions 28 and the Heck reaction. 29 The recognition of diethyl amine as a catalyst, first by Knoevenagel, 1 paved the way for the development of a large number of catalysts [30][31][32][33] and reaction conditions. [34][35][36] Despite the various methods, the Knoevenagel condensation is a simple and straightforward approach for the synthesis of acrylonitrile derivatives.…”