Ceric Ammonium Nitrate (CAN)–Catalyzed Multicomponent Reactions: An Efficient Catalyst for Green Organic Synthesis

Abstract

The multicomponent reactions (MCRs) consist of two or more synthetic steps which are carried out without isolation of any intermediate thus reducing time, saving money, energy and raw materials. The development of MCRs in the presence of Ceric Ammonium Nitrate (CAN) is an efficient approach that meets with the requirements of sustainable chemistry. The aim of this review is to highlight the interactive effect of the combined use of MCRs and CAN for the development of new eco-favourable methodologies for synthetic organic chemistry. Many advantages for the use of CAN as a catalyst in organic synthesis, such as, a very small amount of this catalyst is enough to complete the reactions in most cases, lower costs, eco-friendly nature, ease of handling, non-toxicity, high reactivity.

Copper-Assisted Direct Nitration of Cyclic Ketones with Ceric Ammonium Nitrate for the Synthesis of Tertiary α-Nitro-α-substituted Scaffolds

“…Ceric ammonium nitrate (CAN) has been widely applied in organic synthesis, especially as a special single-electron-transfer oxidant . Due to its low toxicity, low cost, safety, air and moisture stability, and ease of handling, it has received increasing attention in recent decades.…”

“…Based on the above-mentioned experimental results and the reported literature, − a possible reaction mechanism was proposed (Scheme ). First, the CAN served as a Lewis acid , to promote the formation of the enolized intermediate I , which was easily oxidized by CAN to generate radical II . The resulting radical II either was directly trapped by NO 2 derived from CAN without Cu species or reacted through the possible intermediate IV stabilized by Cu species to afford the desired product 2a .…”

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

“…The reaction of aldehydes 1 with dimedone 72 and ammonium acetate or aniline derivatives in the presence of different catalysts and solvents afforded 5 H ‐acridine‐1,8‐dione derivatives 131 (Methods A‐E, Scheme , Table ) …”

“…The reaction of aldehydes 1 with dimedone 72 and ammonium acetate or aniline derivatives in the presence of different catalysts and solvents afforded 5H-acridine-1, 8-dione derivatives 131 (Methods A-E, Scheme 73, Table 19). [49,66,[147][148][149] Fekri et al [147] have reported that a one-pot, multicomponent reaction of bis(aldehydes) 132, dimedone 72, and ammonium acetate in the presence of a catalytic amount of nano particle Fe 3 O 4 afforded bis(1-phenyl-1Hpyrazole-4,3-diyl))bis(3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione derivatives 133 in good yields (Scheme 74).…”

Four component synthesis of highly functionalized pyrano[2,3-c]pyrazoles from benzyl halides

“…Therefore, synthetic organic chemists focused their attention toward designing reactions by following the principles of green chemistry. [1] This has been achieved by solvent free reaction conditions that eliminates the use of hazardous solvents. [2] Multicomponent reactions are also eco-friendly and efficient green tools as they offer significant advantage such as minimization of waste.…”