B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of: In situ -formed enamines
A highly efficient B(C6F5)3-catalyzed tandem protonation/deuteration and reduction of in situ-formed enamines in the presence of water and pinacolborane was developed. Regioselective β-deuteration of tertiary amines was achieved with high chemo- and regioselectivity. D2O was used as a readily available and cheap source of deuterium. Mechanistic studies indicated that B(C6F5)3 could activate water to promote the protonation and reduction of enamines. This journal is
Wu, Rongpei,Gao, Ke
p. 4032 - 4036
(2021/05/19)
Multicomponent and one-pot synthesis of trisubstituted pyridines through a Pd-catalyzed cross-coupling/cross-coupling/cycloaddition sequence
Trisubstituted pyridines are regioselectively synthesized through multicomponent and one-pot processes promoted by a bifunctional Pd-catalyst. The process involves formation of an enamine by Pd-catalyzed amination of an alkenyl bromide, formation of a 2-aza-1,3-butadiene by Pd-catalyzed cross-coupling of a trimethylsilylimine with an alkenyl bromide, and Lewis acid catalyzed cycloaddition between the enamine and the azadiene.
Barluenga, José,Jiménez-Aquino, Agustín,Fernández, M. Alejandro,Aznar, Fernando,Valdés, Carlos
p. 778 - 786
(2008/04/12)
ALDEHYDE-ENAMINES FROM α-OXOCARBOXYLIC ACIDS. A FACILE AND GENERAL ROUTE TO ALDEHYDES VIA DECARBOXYLATION OF α-OXOCARBOXYLIC ACIDS CARRYING β-HYDROGENS
When α-oxocarboxylic acids carrying β-hydrogens are treated with a secondary amine in boiling benzene with azeotropic removal of water, they decarboxylate quantitatively to form aldehyde-enamines which subsequently are hydrolyzed to the corresponding aldehydes in high yields.
Stamos, Ioannis K.
p. 459 - 462
(2007/10/02)
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