Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• functionalization with nitrogen nucleophiles, including amides, sulfonamides and primary arylamines. In addition, the oxazole-based DG could be easily deprotected to provide the corresponding benzoic acid 44 by heating in EtOH in the presence of KOH (Scheme 13). As another easily available N-containing aromatic

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

• George Iakobson,
• Junyi Du,
• Alexandra M. Z. Slawin and
• Petr Beier

Beilstein J. Org. Chem. 2015, 11, 1494–1502, doi:10.3762/bjoc.11.162

• ][58], Lewis acid catalyzed electrophilic borylations of electron-rich arenes [59][60][61][62], and Sandmeyer-type borylation of arylamines or diazonium salts with B2pin2 [63][64][65][66][67], B2(OH)4 [68] or R2N-BH2 [69]. Several attempts were made to synthesize the SF5-phenylboronates. Patent

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• used readily available N-(o-halobenzyl)arylamines as starting materials [17]. The o-haloarylbenzylamines (obtained by nucleophilic substitution of various anilines with 2-iodobenzyl chloride) gave the corresponding amide anions by an SRN1 substitution reaction in NH3 or DMSO as solvent under

• -halobenzyl)arylamines, oxime carbonates, isocyanobiphenyls, etc.). Phenanthridines are usually obtained within 2–3 reaction steps, by application of different radical initiators. An intriguing alternative is the radical generation by UV irradiation with or even without a photocatalyst. The major advantage of

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• concluded that the oxidative arylamination of 1,5-DHN (1) is favorable with arylamines containing electron-donor substituents. Bearing in mind that the formation of the quinone monoimines 6–10 under the above experimental conditions requires aerial oxidation reactions, most likely mediated by oxygen species

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Mimoza Gjikaj and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170

• reaction of the mercaptoacetates 3 and 5 with 2.1 equivalents of various arylamines is the key step of our thiazolidin-4-one synthesis, that led to the corresponding (Z)-3-aryl-2-(2,3,3-trichloro-1-nitroallylidene)thiazolidin-4-ones 7–18 with up to 81% yield. As an example for the sequential reactivity of

Silver and gold-catalyzed multicomponent reactions

• Giorgio Abbiati and
• Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

• arylamines 72 and alkylaldehydes 73 to avoid decomposition [95]. Scheme 35 shows the general reaction outcome for both processes. The two main features of the reported three-component Ag-catalyzed process are (i) the mild reaction conditions and (ii) the high degree of diastereo- and enantioselectivity. The

• arylamines 72 bear an o-thiomethyl and a p-methoxy substituent instead of a single o-methoxy substituent. The corresponding electron-rich aldimines are less electrophilic and subsequently more stable under the reported reaction conditions. Moreover, the authors report on a more effective association of the

Synthesis, characterization and luminescence studies of gold(I)–NHC amide complexes

• Adrián Gómez-Suárez,
• David J. Nelson,
• David G. Thompson,
• David B. Cordes,
• Duncan Graham,
• Alexandra M. Z. Slawin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2013, 9, 2216–2223, doi:10.3762/bjoc.9.260

• straightforward methodology for the synthesis of gold(I)–amide complexes. Results and Discussion Synthesis and characterization of gold(I)–amide complexes We began our studies by exposing hydroxide 1 to a series of alkyl- and arylamines. While no reaction was observed with either morpholine or isopropylamine, the

An organocatalytic route to 2-heteroarylmethylene decorated N-arylpyrroles

• Alexandre Jean,
• Jérôme Blanchet,
• Jacques Rouden,
• Jacques Maddaluno and
• Michaël De Paolis

Beilstein J. Org. Chem. 2013, 9, 1480–1486, doi:10.3762/bjoc.9.168

• dichloromethane were used for this work. Following our procedure [13], catalyst 6 was prepared from (±)-1-benzyl-3-aminopyrrolidine [18471-40-4]. N-Arylimino ethyl glyoxylates 2a–c were prepared by a condensation of ethyl glyoxylate and arylamines in toluene (c = 1 M) with MgSO4 at room temperature. IBX (2

Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction

• Ashish Sharma,
• Mrityunjay Singh,
• Nitya Nand Rai and
• Devesh Sawant

Beilstein J. Org. Chem. 2013, 9, 1235–1242, doi:10.3762/bjoc.9.140

• imine in situ. The intermediate imine then undergoes a 6-endo cyclization to furnish the cyclized product, tetrahydro-β-carboline [10]. Recently, arylamines have been employed instead of the aliphatic amines for the Pictet–Spengler reaction. These reactions are generally termed as modified Pictet

Synthesis of functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] via one-pot four-component reactions

• Li-Juan Zhang,
• Qun Wu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 846–851, doi:10.3762/bjoc.9.97

• Li-Juan Zhang Qun Wu Jing Sun Chao-Guo Yan College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.9.97 Abstract In the presence of triethylamine as catalyst, the one-pot four-component reactions of arylamines, methyl propiolate, isatin and

• arylamines and other primary amines. Keywords: 1,4-dihydropyridine; electron-deficient alkyne; four-component reaction; isatin; one-pot reaction; spiro compound; Introduction β-Enaminones and β-enamino esters represent important synthetic building blocks for the development of versatile carbon–carbon bond

• reactions of arylamines, methyl propiolate, aromatic aldehydes and malononitrile (ethyl cyanoacetate) and successfully developed a facile synthetic procedure for functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones]. Results and Discussion The efficient formation of

Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach

• Sandeep Kumar,
• Ramendra Pratap,
• Abhinav Kumar,
• Brijesh Kumar,
• Vishnu K. Tandon and
• Vishnu Ji Ram

Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92

• group as well as by Wittig reaction [23][24]. The growing importance of 3-alkenylindolin-2-ones has resulted in the design of numerous new synthetic routes. Recently, metal-catalyzed carbonylative annulation of alkynyl-arylamines has been employed for the synthesis of this class of compounds [25][26][27

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• cyclopentane-1,3-dione. Under similar conditions various arylamines and isatins with different substituents reacted with cyclopentane-1,3-dione in acetic acid at room temperature for 8–10 hours to afford the corresponding spiro[dihydropyridine-oxindole] compounds 1a–1k in good yields. The results are shown in

• of spiro[dihydropyridine-oxindole] 1b. The two kinds of spiro compounds from reactions of isatins with arylamines and cyclic 1,3-diketones. Molecular structure of spiro[dihydropyridine-oxindole] 2f. Molecular structure of compound 3d. The four-component reactions containing dimedone (a) and

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

• Jing Sun,
• Hong Gao,
• Qun Wu and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2012, 8, 1839–1843, doi:10.3762/bjoc.8.211

• Jing Sun Hong Gao Qun Wu Chao-Guo Yan College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.8.211 Abstract In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol

• was prepared in 63% yield (Scheme 1). The tetrahydroquinoline was obviously formed by the reaction of the previously formed β-enamino ester with in situ generated N-aryl aldimine. Thus, a domino Povarov reaction is successfully established. Similarly, various arylamines and aromatic aldehydes were

• used in the reaction under the same conditions. The results are summarized in Table 1. All the reactions proceeded smoothly to afford the corresponding functionalized tetrahydroquinolines (1a–1m) in moderate to good yields (41–67%). Arylamines and aromatic aldehydes with an electron-donating alkyl or

Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides

• Marco Caricato,
• Nerea Jordana Leza,
• Claudia Gargiulli,
• Giuseppe Gattuso,
• Daniele Dondi and
• Dario Pasini

Beilstein J. Org. Chem. 2012, 8, 967–976, doi:10.3762/bjoc.8.109

• vicinal phenol moieties (which compete since they are comparable in nucleophilicity with aromatic amines) are rare [32][33]. As already reported [31], test reactions on model compounds gave disappointing results. The use of benzylic amines, more nucleophilic than arylamines, and therefore competing less

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

• Nan Sun,
• Bin Li,
• Jianping Shao,
• Weimin Mo,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2012, 8, 61–70, doi:10.3762/bjoc.8.6

• with TCT. Because inorganic bases were more efficient during the conversion of arylamines to N-aryl dithiocarbamates in aqueous systems [54][55][56][57][58][59], we chose inorganic bases to screen the optimal reaction conditions for the one-pot synthesis of 4. Following the literature procedure, N

•  2. As can be seen from Table 2, all tested alkylamines and electron-rich arylamines afforded their corresponding isothiocyanates in excellent yields (Table 2, entries 1–13). Compared to arylamines, alkylamines can generally be converted into their corresponding dithiocarbamates in a relative short

• similar activity as linear alkylamines (Table 2, entries 1–9). The relative low yields of isopropyl isothiocyanate and tert-butyl isothiocyanate were ascribed to their volatility loss associated with isolation (Table 2, entries 1 and 3). The substituent pattern on the phenyl ring of arylamines exhibited

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• step. Xi and co-workers developed an elegant one-pot synthesis of 2-alkynylindoles 64 involving o-bromo-(2,2-dibromovinyl)benzenes 63, arylamines and terminal alkynes as starting partners [36]. It should be noted that the three components are present at the same time in the reaction system and the best

• derivatives. This one-pot procedure worked with a wide variety of primary amines including allyl-, benzyl-, alkyl- and arylamines, and antipsychotic promazine as well as some analogues 74 were synthesized when 3-(dimethylamino)-1-propylamine (73) was used as the amine component (Scheme 31). Amines as coupling

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• obtained in all cases. A similar Markovnikov hydroamination [59] could also be achieved via an intermolecular hydroamination of allenamides 123 with arylamines under mild AuPPh3OTf catalysis conditions to furnish allylamino (E)-enamides stereoselectively (Scheme 22). Hesp and co-workers have identified a

Conjugated polymers containing diketopyrrolopyrrole units in the main chain

• Bernd Tieke,
• A. Raman Rabindranath,
• Kai Zhang and
• Yu Zhu

Beilstein J. Org. Chem. 2010, 6, 830–845, doi:10.3762/bjoc.6.92

• copolymerized with primary or secondary arylamines to yield DPP-containing polyiminoarylenes. The solutions of the polymers in chloroform exhibited a purple red colour with absorption maxima between 530 and 550 nm, and emission maxima from 610 to 630 nm. Fluorescence quantum yields were moderate (20 to 60

Suzuki–Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene–palladium complex catalyst

• Guangming Nan,
• Fang Ren and
• Meiming Luo

Beilstein J. Org. Chem. 2010, 6, No. 70, doi:10.3762/bjoc.6.70

• halides [19][20][21][22][23][24][25][26][27][28]. However, arenediazonium salts are prone to decompose upon storage, which restricts their practical use. Recently, 1-aryltriazenes, which are stable and can be easily prepared from the corresponding arylamines, have been employed by Tamao et al. as

N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system

• Zhang-Guo Zheng,
• Jun Wen,
• Na Wang,
• Bo Wu and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2008, 4, No. 40, doi:10.3762/bjoc.4.40

• copper-mediated N-arylation reaction plays an important role in organic synthesis since the resultant products, arylamines and N-arylheterocyclic compounds, are ubiquitous compounds in pharmaceuticals, crop-protection chemicals and material science [1][2][3][4]. In 1997, the copper-mediated heteroatom

Expedient syntheses of the N-heterocyclic carbene precursor imidazolium salts IPr·HCl, IMes·HCl and IXy·HCl

• Lukas Hintermann

Beilstein J. Org. Chem. 2007, 3, No. 22, doi:10.1186/1860-5397-3-22

• imidazolium salts by condensation of glyoxal, two equivalents of aliphatic or aromatic amine, and an equivalent of paraformaldehyde in the presence of hydrochloric acid was reported by Arduengo in a patent in 1991 (Scheme 1a). [5] It is successful for a range of alkyl- and arylamines, but the original