Abstract
A new robust heterogeneous, versatile, an environmentally benign, eco-friendly, recyclable CuFAP catalyst has been developed for the direct synthesis of nitriles and amides from aldehydes at 100°C for 6 h and 4 h, respectively, under neat reaction condition using hydroxylamine hydrochloride in the presence and the absence of tosyl chloride, respectively. Also the recyclability of catalyst as well as influence of solvents, additives on catalysts performance was investigated. The protocol can be considered as an alternative to conventional method for the synthesis of nitriles and amides in good to excellent yields. A highlight of our protocol is the easy separation of catalyst from reaction mixture, hence the catalyst is reused several times without significant loss of its catalytic activity.
Highlights
The nitriles and amides are versatile prolific moieties acting as major building blocks in organic chemistry to synthesise numerous nitrogen-containing heterocyclic compounds which are integral part of fine chemicals, agrochemicals, polymer and medicinally and biologically potent compounds
A new robust heterogeneous, versatile, an environmentally benign, eco-friendly, recyclable CuFAP catalyst has been developed for the direct synthesis of nitriles and amides from aldehydes at 100 ̊C for 6 h and 4 h, respectively, under neat reaction condition using hydroxylamine hydrochloride in the presence and the absence of tosyl chloride, respectively
Owing to the potential applications of nitriles in pharmaceuticals, agricultural chemicals, polymer, dyes [6], various methods for its synthesis such as classic Sandmeyer reaction [7] [8] [9] [10] [11], or nucleophilic substitution of aryl halides with metal cyanide [12] [13] [14] [15], dehydration of aldoximes [16] [17] [18] [19], dehydration of amide [20] [21] [22] [23], amine to nitrile [24] [25] [26], oxidation of alcohols [27] [28], and direct conversion of aldehydes to nitriles using NH2OH∙HCl [29], and/or ammonia over CuCl2/NaOMe/ O2 [30], Pd(OAc)2 [31], Oxone [32], H2O2 [33], I2 [34], NBS [35], IBX [36], NaICl2 [37], p-TSA [38], KF/Al2O3 [39], catalysts have been well documented
Summary
The nitriles and amides are versatile prolific moieties acting as major building blocks in organic chemistry to synthesise numerous nitrogen-containing heterocyclic compounds which are integral part of fine chemicals, agrochemicals, polymer and medicinally and biologically potent compounds. Even though significant progress has been achieved, almost all of these approaches developed so far for the synthesis of nitriles and amides suffer from one or other major limitations and drawbacks such as drastic reaction conditions, high temperature, long reaction time, and low yield to desired products. In addition to these limitations, use of non-recoverable, moisture sensitive, toxic, corrosive, expensive reagents and catalysts such as HCN/metal cyanides, metal/enzyme etc. As part of our continuous studies toward development of cost effective, eco-friendly heterogeneous recyclable catalysts for the organic transformation, [68]-[73] we report a simple, novel, solvent free, cost effective protocol using non-toxic, non-corrosive, stable, recyclable, eco-friendly robust heterogeneous CuFAP catalyst for the facile one pot synthesis of a wide range of nitriles and amides from the various aldehydes (Scheme 1), which may be a practical approach for the synthesis of various nitriles and amides
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