Zn(BH4)2/Al2O3: A new synthetic method for efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols

Abstract

Zn(BH4)2 (0.5-2 mmol) in the presence of Al2O3 (1 mmol) reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α, β-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in THF at room temperature in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system

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.…”

Regioselective and Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds by NaBH4Mohamadi1, Setamdideh2, Khezri3 2013Organic Chemistry InternationalSelf Cite9060View full textAdd to dashboardCite

“…To control the reducing potential and selectivity of metal hydrides specially NaBH 4 (common reducing agent) for the 1,2-reduction of conjugated carbonyl compounds, numerous hydroborate agents have been developed in the following ways: (a) by the replacement of hydride(s) with bulky substituents or electron-withdrawing/releasing groups in order to discriminate between the structural and electronic environments of carbonyl groups [4][5][6][7]; (b) combination with Lewis acids [8][9][10] such as Luche reduction [11,12] and mixed solvent systems [1,2]; (c) use of transition metal hydroborates and their new modifications [13], (d) use of phosphonium tetrahydroborates [14,15], and finally (e) immobilization on an anion exchange resin [16]. In this context and continuation of our studies for the reduction of functional groups in organic synthesis [17][18][19][20], we decided to apply NaBH 4 /Ba(OAc) 2 as new a reducing system for reduction of , -unsaturated carbonyl compounds. Now we wish to report an efficient method for the regioselective reduction of , -unsaturated aldehydes and ketones by NaBH 4 /Ba(OAc) 2 as a new reducing system.…”

Utility of Lauroyl Isothiocyanate as a Scaffold in the Synthesis of Some Novel Pyrimidine Derivatives and Their Antimicrobial Assessment

“…Furthermore, the presence of carbonyl group in acyl isothiocyanates imparts unique reactivity to them; leading to the synthesis of biologically important heterocyclic skeletons such as thiazoles, benzimidazoles, triazoles, dithiolane, thiadiazoles, pyrimidines, fused pyrimidines, fused oxazolines, triazines, and oxazines. [10][11][12][13][14][15][16][17] Pyrimidine and fused pyrimidine derivatives are a class of important heterocycles that have attracted considerable attention due to their therapeutic and pharmacological properties such as anticancer, 18,19) antiviral, 20) antihypertensive, 21) analgesic, 22,23) antiinflammatory, 24) antifungal and antibacterial. 25) In the light of previous observations and benefits, and in continuation of our previous work [10][11][12] in developing synthetic strategies for synthesis of fused heterocyclic compounds, lauroyl isothiocyanate reacted with a starting material containing enaminonitrile moiety to give polynuclear heterocyclic compounds containing pyridazine, thiophene, pyrimidine, benzimidazole, 1,2,4-triazole, 1,3,5-triazine and 1,3-oxazine rings.…”