Reductive amination of aldehydes with sodium borohydride and lithium aluminum hydride in the presence of lithium perchlorate

Abstract

A one-pot high yielding reductive amination of aldehydes with primary and secondary amines using LiClO 4 /NaBH 4 and LiClO 4 /LiAlH 4 as reducing agents in diethyl ether is described.

Synthesis and antibacterial activity of Schiff bases and amines derived from alkyl 2-(2-formyl-4-nitrophenoxy)alkanoates

“…The first method involves catalytic hydrogenation with platinum, palladium, ruthenium, cobalt or nickel catalysts (Klyuev and Khidekel, 1980 ; Petrisko and Krupka, 2005 ; Tripathi et al , 2008 ). The second method utilizes metal hydride reagents, mainly sodium borohydride (Panfilov et al , 2000 ), sodium triacetoxyborohydride (Abdel-Magid and Mehrman, 2006 ; Gribble, 2006 ), sodium or lithium cyanoborohydride (Borch et al , 1971 ; Grenga et al , 2009 ), and sodium borohydride modified with numerous polyvalent metal salts (Saxena et al , 2000 ; Saidi et al , 2007 ; Neidigh, et al , 1998 ) or activated by acids (Cho and Kang, 2005 ; Alinezhad et al , 2010 ).…”

NaBH4/C: A Convenient System for Reductive Amination of Aldehydes

“…Because, other approaches such as: the reduction of nitro, cyano, azide, carboxamide compounds or the alkylation of amines are often problemssuch as: harsh reaction conditions, overalkylation, low chemical selectivity and generally poor yields. The reductive aminationreactionhas been carried out by sodium borohydridewith different reducing system [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] .But, in continuing our efforts for the development of new reducing systems [16][17][18][19][20][21][22][23][24][25][26][27][28] ,in this context, we have reported the reductive amination reaction of aldehydes with anilines by NaBH 4 /C system in THF.…”

Micellar media catalyzed highly efficient reductive amination of carbonyl compounds with bis(triphenylphosphine)(tetrahydroborato)zirconium(II), [Zr(BH4)2(Ph3P)2], as a new and a highly water tolerant tetrahydroborate reducing agent

“…Toxic zinc-modified cyanotrihydroborate [17] and sodium triacetoxyhydroborate Na[BH(OAc) 3 ] [18] have been applied for reductive amination in acidic media which limits the application of these reagents for acid sensitive substrates. Recently, application of NaBH 4 and a modified zinc borohydride for reductive amination of carbonyl compounds is reported [19].…”