Hydroamination, the addition of HNR2across a carbon-carbon π bond, is in principle one of the most atom-economical methods for the synthesis of this class of compounds. Sodium and lithium metals are preferred over the others available. Journal of the American Chemical Society 2015 , 137 (30) , 9716-9721. Reaction mechanism. Hydroamination Reactions of Alkenes. The first reaction step involves 1,4-addition of the catalytic tertiary amine to the activated alkene to generate the zwitterionic aza-enolate. Catalytic hydroaminations of alkenes, allenes, and dienes (which may be inter- or intramolecular) afford amines, i… As a consequence of the importance of nitrogen-containing compounds in biological and pharmaceutical applications, methods for the construction of carbon-nitrogen bonds have been heavily studied for at least 150 years. Hydroamination is most … It is a form of hydrofunctionalization with the functional group being an amine or amino derivative. Viable substrates for these reactions include unactivated alkenes, vinyl arenes, allenes, and strained alkenes. Hoffmann first proposed a mechanism for the MBH reaction. Design of Modified Amine Transfer Reagents Allows the Synthesis of α-Chiral Secondary Amines via CuH-Catalyzed Hydroamination. Studies have shown the … Hydroamination reactions of alkenes represent additions of N-H bonds across carbon-carbon double bonds. Hydroamination is a reaction that involves the addition of a hydrogen and an amino group across an unsaturated C-C bond, such as that in alkenes or in alkynes. In the second step, this enolate adds to an aldehyde via an aldol addition. Alkene activation by co-ordination to the metal followed by amine attack was the mechanism that was proposed . Base-catalyzed hydroamination reactions using alkali-earth metals are more economical because of the lower price of alkali metal derivatives compared to transition metals.
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