Metal-free enaminone C–N bond cyanation for the stereoselective synthesis of ( <i>E</i>)- and ( <i>Z</i>)-β-cyano enones

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Abstract

The C–N bond cyanation of tertiary enaminones has been realized for the stereoselective synthesis of both ( E)- and ( Z)-β-cyano enones under mild metal-free conditions, providing highly practical approaches for the synthesis of β-cyano enones.

Abstract

A highly practical method for C–CN bond formation by C–N bond cleavage on enaminones leading to the efficient synthesis of β-cyano enones is developed. The reactions take place efficiently to provide ( E)-β-cyano enones with only a molecular iodine catalyst. In addition, the additional employment of oxalic acid enables the selective synthesis of ( Z)-β-cyano enones.

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Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.

Anup Bhunia, Santhivardhana Yetra, Akkattu Biju (2012)

This tutorial review is aimed at highlighting recent developments in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions utilizing a versatile class of reactive intermediates, viz., arynes, which hold the potential for numerous applications in organic synthesis. Key to the success of the resurgence of interest in the rich chemistry of arynes is primarily the mild condition for their generation by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates. Consequently, arynes have been employed for the construction of multisubstituted arenes with structural diversity and complexity. The versatile transition-metal-free applications of arynes include cycloaddition reactions, insertion reactions and multicomponent reactions. In addition, arynes have found applications in natural product synthesis. Herein, we present a concise account of the major developments that occurred in this field during the past eight years.