Coupling reactions of aldehydes, amines and

Interestingly, the alkenylation of sp3 C-H bond is observed in the iridium-catalyzed coupling reaction of aldehydes, amines, and alkynes (Equation (56)).62... 

Indium-Catalyzed, Three-Component Coupling Reactions of Aldehydes, Amines and Alkynes 253... 

The ionic liquid [BMIM]BF4 was found to efficiently catalyze the three-component coupling reactions of aldehydes, amines, and homophthalic anhydride under ambient conditions to give the corresponding c/ -isoquinolonic acids in excellent yields with... 

Shiraishi, H., Nishitani, T., Sakaguchi, S. and Ishii, Y., Preparation of substituted alkylpyrroles via samarium-catalyzed three-component coupling reaction of aldehydes, amines, and nitroalkanes, /. Org. Chem., 1998, 63, 6234-6238. 

Sc(OTf)3-catalyzed three-component coupling reactions of aldehydes, amines, and dienes have been examined. In the presence of 10 mol % Sc(OTf)3 and magnesium sulfate, benzaldehyde was treated with aniline and Danishefsky s diene. The desired three-component reaction proceeded smoothly to afford the corresponding tetrahydropyridine derivative in 83 % yield (Eq. 9) [24b]. Under the same reaetion conditions, cyclopentadiene was used instead of Danishefsky s diene to afford the corresponding tetrahydroquinoline derivative (Eq. 10). Different combinations of aldehydes, amines, and alkenes are possible in these reactions, and afford diverse tetrahydroquinoline derivatives in high yields. 

It was recently found that three-component coupling reactions of aldehydes, amines, and silyl enolates proceeded smoothly in micellar systems with Sc(OTf)3 as catalyst [70]. In a typical procedure, the amine and 1-phenyl-l-trimethylsiloxyethene were combined in the presence of Sc(OTf)3 (5 mol %) in 35 mM SDS, and the aldehyde was then added. The reaction proceeded smoothly at room temperature to afford the corresponding /3-amino ketone derivative in 87 % yield. It is reported that the dehydration (imine formation) and the coupling of two water-unstable substrates,... 

Table 14-13. Three-component coupling reactions of aldehydes, amine, and silyl enol ethers.

The effectiveness of lanthanide Lewis acid in Mannich-type reaction was further highlighted by three-component coupling reaction of aldehydes, amines, and enol silyl ethers [7]. With MS 4A or MgS04 as dehydrating agent, 5-10 mol% ofYb(OTf)3 worked well to afford corresponding -amino ketone and esters in good to excellent yield (Table 13.3). It should be noted that the present reaction conditions were... 

Wang reported three-component coupling reaction of aldehydes, amines, and dienes by lanthanide triflate catalyzed aza-Diels-Alder reaction in water [35, 36]. Among lanthanide triflates screened, lanthanum, praseodymium, neodymium, and ytterbium triflate were found to be effective (Table 13.16). It is worth noting that aqueous formaldehyde could be employed as substrate. These reaction conditions were applied in the synthesis of aza-sugars. 

Catalytic coupling reaction of aldehydes, alkynes, and secondary amines promoted by less than 3 mol.% of Ag(l) salt was reported by Li et al,517 In this reaction, pure water was used as solvent and Agl was found to be the best catalyst without need of any additives or co-catalysts (Table 9). The reaction mechanism has been proposed as shown in Scheme 110. 

Kobayashi S, Ishitani H, Nagayama S (1995) Ln(OTf)3- or Sc(OTf)3-catalyzed three components coupling reactions between aldehydes, amines, and dienes or alkenes efficient synthesis of pyridine and quinoline derivatives. Chem Lett 423 f24... 

Aminoalkyl and Related Acids. - Further development of the classical three component approach to aminoalkylphosphonates (the Kabachnik-Fields reaction) has been reported. The reaction of aldehydes, hydroxylamines and dimethyltrimethylsilyl phosphite using lithium perchlorate/diethyl ether as a catalyst gives N-trimethylsilyloxy-a-aminophosphonate derivatives. The catalytic activities of various lanthanide triflates as well as indium trichloride have been examined for the Kabachnik-Fields type reactions of aldehydes, amines and the phosphorus nucleophiles HP(0)(0Et)2 and P(OEt)3 in ionic liquids. TaCb-Si02 has been utilized as an efficient Lewis acid catalyst for the coupling of carbonyl compounds, aromatic amines and diethyl phosphite to produce a-... 

At a loading as low as 0.5 mol%, indium triflate catalyzes the three-component coupling reaction between aldehydes, amines, and Danishefsky s diene to afford tetrahydropyridine derivatives (Scheme 8.106) [138]. In fhe presence of indium triflate, 3,4-dihydro-2H-pyran reacts with in sitw-generated chromone Schiff s bases to give the endo cycloadducts (Scheme 8.107) [139]. 

Bearing in mind the usefulness and efficiency of one-pot procedures, three-component coupling reactions between aldehydes, amines, and alkenes via imine formation and imino Diels-Alder reactions were examined by using Ln(OTf )3 as a catalyst. 

Thus, a new type of Lewis acid, lanthanide triflates, is quite effective for the catalytic activation of imines, and has achieved imino Diels-Alder reactions of imines with dienes or alkenes. The unique reactivities of imines which work as both dienophiles and azadienes under certain conditions were also revealed. Three-component coupling reactions between aldehydes, amines, and dienes or alkenes were successfully carried out by using Ln(OTf)3 as catalysts to afford pyridine and quinoline derivatives in high yields. The triflates were stable and kept their activity even in the presence of water and amines. According to these reactions, many substituted pyridines and quinolines can be prepared directly from aldehydes, amines, and dienes or alkenes. A stepwise reaction mechanism in these reactions was suggested from the experimental results. 

M. Kidwai, V. Bansal, A. Kumar, S. Mozumdar, Green Chem. 2007, 9, 742-745. The first Au-nanoparticles catalyzed green synthesis of propargylamines via a three-component coupling reaction of aldehyde, alkyne and amine. 

Das et al. [29] developed a simple, efficient, cost-effective, and metal-free four-component coupling reaction of aldehydes, amines, dialkyl acetylenedicaiboxyl-ates, and nitromethane for the synthesis of corresponding 1,2,3,4-tetra-substituted pyrroles 6 using molecular iodine as a catalyst (Scheme 10.4). 

Das B, Bhunia N, Lingaiah MA (2011) Simple and elficient metal-free synthesis of tetra-substituted pyrroles by iodine-catalyzed four-component coupling reaction of aldehydes, amines, dialkyl acetylenedicarboxylates, and nitromethane. Synthesis 2011 3471-3474 Khan AT, Ghosh A, Khan MM (2012) One-pot four-component domino reaction for the synthesis of substituted dihydro-2-oxypyrrole catalyzed by molecular iodine. Tetrahedron Lett 53 2622-2626... 

SbCls adsorbed on AI2O3 has been found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl and aliphatic amines, esters of S-a-amino acids) with dialkylphosphites to afford the corresponding a-amino-phosphonates in high yields (Scheme 49). ... 

Scheme 17 Iron-catalyzed three-component coupling reactions of aldehydes, terminal alkynes, and amines...

To check the scope of this coupling reaction, a study with different combinations of aldehydes, amines, and terminal alkynes was performed. Aromatic alkynes turned out to be more reactive than aliphatic ones. This study included aliphatic... 

Trifluoroethanol is an efficient and recyclable solvent in helping one-pot, three-component coupling reactions of aldehydes or ketones, amines, and trimethyl-silyl cyanide or trimethyl phosphate to yield the corresponding a-amino nitriles or a-amino phosphonates in high yields (Equation 4.18). This method does not require the use of either an add or base catalyst [40],... 

Three component coupling reactions of aldehydes or ketones, amines, and elemental sulfur - called Willgerodt-Kinder reactions - are used to synthesize various thioamides, although the protocol of this reaction was reported over 80 years ago. However, the reaction procedure has been developed. For example, the reaction of dialdehydes, diamines and sulfur was investigated for the preparation of poly thioamides 12 (Eq. 1) [12]. 

Recently, Chi and co-workers reported a highly enantioselective oxidative coupling reaction of aldehydes 14 with tertiary amines 13 under cooperative... 

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