Gold Catalyzed Multicomponent Reactions beyond A3 Coupling

Abstract

The preparation of complex architectures has inspired the search for new methods and new processes in organic synthesis. Multicomponent reactions have become an interesting approach to achieve such molecular diversity and complexity. This review intends to illustrate important gold-catalyzed examples for the past ten years leading to interesting skeletons involved in biologically active compounds.

Recent advances in the iron‐catalysed multicomponent reactions

“…Shaabani and co‐workers put forward a three‐component strategy for the synthesis of 1,6‐dihydropyrazine‐2,3‐dicarbonitrile (Scheme 64) and 3,4‐dihydroquinoxalin‐2‐amine (Scheme 65). [ 21 ] The reaction of 2,3‐diaminomaleonitrile 158 , acetone and cyclohexyl isocyanide 16 in presence of iron catalyst in 6 ml water resulted in the formation of the desired product 1,6‐dihydropyrazine‐2,3‐dicarbonitrile 159 with a maximum of 93% yield. The reaction of o ‐phenylene diamine with acetone and cyclohexyl isocyanide delivered 3,4‐dihydroquinoxalin‐2‐amine 161 in 92% yield.…”

“…disclosed the synthesis of tetrahydro‐1 H ‐1,5‐benzodiazepine‐2‐carboxamide 167 (Scheme 68) and 4,5,6,7‐tetrahydro‐1 H ‐1,4‐diazepine‐5‐carboxamide 168 (Scheme 69) by using natural wool sulfonic acid (wool‐SO 3 H) and wool‐supported Fe 3 O 4 nanoparticles (nano‐Fe 3 O 4 @wool) as catalyst. [ 21 ] The substrate scope exploration using different amines and carbonyl compounds revealed that these have reacted well to give the desired products in good to excellent yields.…”

“…Hantzsch dihydropyridine synthesis, [ 6,7 ] Biginelli reaction, [ 8,9 ] Passerini reaction, [ 10,11 ] Kabachnik‐Fields reaction, [ 12,13 ] Ugi reaction, [ 14,15 ] Gröbcke‐Blackburn‐Bienaymé reaction [ 16 ] etc. Transition metal catalysis also made its way into multicomponent reactions and different transition metals like Pd, [ 17 ] Cu, [ 18,19 ] Rh, [ 20 ] Au, [ 21 ] Ag, [ 22 ] Zn, [ 23 ] Fe [ 24,25 ] etc. have shown its applicability in MCRs.…”

A3 Coupling Reaction in the Synthesis of Heterocyclic Compounds

“…Many of them highlight the advances in the synthesis of propargylamines, [23] including the asymmetric version of the reaction [17g,23c,24] . Besides, a number of reviews are available on the employment of particular catalysts, e. g ., gold, [25] nanoparticles [26] and so on. Applications of a particular type of starting materials are considered in the review by Liu [27] .…”

The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines

“…Multicomponent reactions (MCRs), defined as one-pot processes in which three or more accessible starting materials are incorporated into a single product without isolating the intermediates, have gained importance in academia and industry [1,2,3,4]. Multicomponent reactions provide numbers of valuable conceptual and synthetic advantages such as sustainability, operational simplicity, and high convergence.…”