Sn‐mediated one‐pot four‐component allylation of aldimines

A convenient and facile method for the synthesis of homoallylic amines was disclosed. The one‐pot reaction of aldehydes, aromatic amines and allylic bromide with tin powder at room temperature could afford the homoallylic amines in good to excellent yield without any promoter or additive. The method is highly efficient and environmentally benign with low cost and concise manipulation. Copyright © 2014 John Wiley & Sons, Ltd.     

Polyaniline‐anchored palladium catalyst‐mediated Mizoroki–Heck and Suzuki–Miyaura reactions and one‐pot Wittig–Heck and Wittig–Suzuki reactions

A polyaniline‐anchored palladium catalyst was prepared and screened for coupling reactions of aryl halides. The robust and recyclable catalyst was effective in Mizoroki–Heck and Suzuki–Miyaura reactions of aryl bromides and aryl iodides. The catalyst system was further employed for one‐pot Wittig–Heck and Wittig–Suzuki combinations to build conjugated compounds in good conversions. Copyright © 2014 John Wiley & Sons, Ltd.     

Silica‐supported Cu(II)–quinoline complex: Efficient and recyclable nanocatalyst for one‐pot synthesis of benzimidazolquinoline derivatives and 2H‐indazoles

The synthesis, characterization and catalytic activity of a Cu(II) complex derived from 2‐oxoquinoline‐3‐carbaldehyde Schiff base supported on amino‐functionalized silica are reported. 3‐(1H‐Benzo[d]imidazol‐2‐yl)quinolines containing piperidine, morpholine and phenylpiperazine skeletons at the C‐2 position were formed in good to excellent yields via the one‐pot reaction of 2‐chloroquinoline‐3‐carbaldehyde, benzene‐1,2‐diamines and secondary amines in the presence of the nanocatalyst under mild conditions. Moreover, the nanocatalyst was found to be recyclable for up to seven runs without significant loss of activity. Also, a series of 2H‐indazoles were synthesized by the catalytic condensation of 2‐bromobenzaldehyde, sodium azide and primary amines.     

Chemoselective one‐pot synthesis of terphenyl derivatives by sequential directed C―H functionalization–Suzuki coupling

A simple and efficient route for the preparation of terphenyl derivatives via palladium‐catalyzed sequential directed C―H arylation/Suzuki–Miyaura cross‐coupling in ‘one‐pot’ has been developed. 4,4′‐(Cyclohexane‐1,1‐diyl)diphenol is an essential ligand. This reaction can tolerate a series of functional groups and provides the terphenyl derivatives in moderate to good yield. Copyright © 2014 John Wiley & Sons, Ltd.     

Functionalized graphene oxide supported copper (I) complex as effective and recyclable nanocatalyst for one‐pot three component synthesis of 1,2,3‐triazoles

Efficient, one pot three‐component reaction of alkyl halides, sodium azide with terminal alkynes can be catalyzed by functionalized graphene oxide with copper(I) under thermal conditions. A series of 1,4‐disubstituted 1,2,3‐triazoles were obtained by this one‐pot strategy. The catalyst was prepared and characterized by Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), emission scanning electron microscopy (FE‐SEM) and energy dispersive X‐ray (EDX). The catalyst can be reused at least five times without significant deactivation.     

A convenient route toward one‐pot multicomponent synthesis of spirochromenes and pyranopyrazoles accelerated via quinolinic acid

In the present work, the catalytic activity of quinolinic acid (QUIN) was studied for the synthesis of spirochromene and pyranopyrazole derivatives from readily available materials. The salient features of these one‐pot multicomponent protocols are the clean reaction profile, easy isolation of products, no chromatographic separation techniques, high efficiency, short reaction time, and high yield of products plus using QUIN as a new, inexpensive, commercially available, and efficient organocatalyst.     

Copper nanoparticles supported on 2‐methoxy‐1‐phenylethanone‐functionalized MCM‐41: An efficient and recyclable catalyst for one‐pot three‐component C–S coupling reaction of aryl halides with benzyl bromide and thiourea

An environmentally friendly copper‐based catalyst supported on 2‐methoxy‐1‐phenylethanone‐functionalized MCM‐41 was prepared and characterized by Fourier transform‐infrared, transmission electron microscopy, field emission‐scanning electron microscopy, X‐ray diffraction and inductively coupled plasma techniques. The catalyst was applied for the one‐pot three‐component C–S coupling reactions of aryl halides with benzyl bromide and thiourea under aerobic conditions to afford the corresponding coupled products in good yields in water. The catalyst could be recovered and recycled five times. These results prove 2‐methoxy‐1‐phenylethanone‐functionalized MCM‐41 supported Cu (II) complex was not leached during the reaction. Also it shows the correct heterogeneous nature of the catalyst.     

Facile synthesis of linear–hyperbranched polyphosphoesters via one‐pot tandem ROMP and ADMET polymerization and their transformation to architecturally defined nanoparticles

A convenient one‐pot synthesis of linear–hyperbranched polyphosphoesters (l–HBPPEs) was accomplished by a tandem ring‐opening metathesis polymerization (ROMP) and acyclic diene metathesis (ADMET) polymerization procedure. A linear monotelechelic poly(norbornene) with a terminal acrylate and many pendent thiol groups is first prepared through adding an internal cis‐olefin terminating agent to the reaction mixture immediately after the completion of the living ROMP, and then utilized as a macromolecular chain stopper in subsequent ADMET polymerization of a phosphoester functional AB₂ monomer, yielding l–HBPPEs as the reaction time prolonged. These l–HBPPEs bearing lots of pendent thiol groups in linear poly(norbornene) and peripheral acrylate groups in HBPPE could be self‐crosslinked in ultradilute solution through thiol‐Michael addition click reaction between acrylate and thiol to give single‐molecule nanoparticles with comparatively uniform size. This facile approach can be extended toward the fabrication of novel nanomaterials with sophisticated structures and tunable multifunctionalities. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 964–972     

Heterograft copolymers via double click reactions using one‐pot technique

The double click reactions (Cu catalyzed Huisgen and Diels–Alder reactions) were used as a new strategy for the preparation of well‐defined heterograft copolymers in one‐pot technique. The synthetic strategy to the various stages of this work is outlined: (i) preparing random copolymers of styrene (St) and p‐chloromethylstyrene (CMS) (which is a functionalizable monomer) via nitroxide mediated radical polymerization (NMP); (ii) attachment of anthracene functionality to the preformed copolymer by the o‐etherification procedure and then conversion of the remaining ? CH₂Cl into azide functionality; (iii) by using double click reactions in one‐pot technique, maleimide end‐functionalized poly(methyl methacrylate) (PMMA‐MI) via atom transfer radical polymerization (ATRP) of MMA and alkyne end‐functionalized poly (ethylene glycol) (PEG‐alkyne) were introduced onto the copolymer bearing pendant anthryl and azide moieties. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 6969–6977, 2008     

Polypyrrole/Fe3O4/CNT as a recyclable and highly efficient catalyst for one‐pot three‐component synthesis of pyran derivatives

Polypyrrole (PPY)/Fe₃O₄/CNT has been synthesized and characterized by FT‐IR, TEM and SEM techniques and its catalytic activity has been evaluated in the synthesis of several series of pyran derivatives. Tetrahydrobenzo[b]pyranes, 4H‐pyran‐3‐carboxylates, 4H,5H‐pyrano[3,2‐c]chromenes and dihydropyrano[2,3‐c]pyrazoles have been successfully prepared from one‐pot three‐component condensation of aldehyde, malononitrile and active methylene‐containing compounds (dimedone /ethyl acetoacetate/4‐hydroxycoumarin/3‐methyl‐2‐pyrazoline‐5‐one) using PPY/Fe₃O₄/CNT as a new and reusable heterogeneous catalyst. The present method offer several advantages such as; high yields of products, short reaction times, easy work‐up procedure and easy separation of the catalyst from the reaction mixture due to its magnetic character. Furthermore, chemoselective synthesis of bis‐benzo[b]pyran from terephthalaldehyde can be achieved by this method.     

One‐pot synthesis of star‐block copolymers using double click reactions

3‐Arm star‐block copolymers, (polystyrene‐b‐poly(methyl methacrylate))₃, (PS‐b‐PMMA)₃, and (polystyrene‐b‐poly(ethylene glycol))₃, (PS‐b‐PEG)₃, are prepared using double‐click reactions: Huisgen and Diels–Alder, with a one‐pot technique. PS and PMMA blocks with α‐anthracene‐ω‐azide‐ and α‐maleimide‐end‐groups, respectively, are achieved using suitable initiators in ATRP of styrene and MMA, respectively. However, PEG obtained from a commercial source is reacted with 3‐acetyl‐N‐(2‐hydroxyethyl)‐7‐oxabicyclo[2.2.1]hept‐5‐ene‐2‐carboxamide (7) to give furan‐protected maleimide‐end‐functionalized PEG. Finally, PS/PMMA and PS/PEG blocks are linked efficiently with trialkyne functional linking agent 1,1,1‐tris[4‐(2‐propynyloxy)phenyl]‐ethane 2 in the presence of CuBr/N,N,N′,N″,N″‐pentamethyldiethylenetriamine (PMDETA) at 120 °C for 48 h to give two samples of 3‐arm star‐block copolymers. The results of the peak splitting using a Gaussian deconvolution of the obtained GPC traces for (PS‐b‐PMMA)₃ and (PS‐b‐PEG)₃ displayed that the yields of target 3‐arm star‐block copolymers were found to be 88 and 82%, respectively. © Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 7091–7100, 2008     

CuBr‐catalysed one‐pot multicomponent synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one derivatives

A novel methodology is presented for the synthesis of 3‐substituted 2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one derivatives based on an efficient tandem multicomponent reaction using copper bromide as catalyst. This methodology is based on the multicomponent one‐pot reaction of methyl 2‐bromobenzoate, phenylisothiocyanate derivatives and sodium azide in the presence of copper bromide and l ‐proline under basic conditions. To show the generality of the method, various phenylisothiocyanates bearing electron‐donating or electron‐withdrawing functionalities were used and the desired products were obtained in high isolated yields.     

Protecting‐group‐free synthesis of glycopolymers bearing thioglycosides via one‐pot monomer synthesis from free saccharides

Polyacrylamides having pendant thioglycosides were successfully synthesized from thioglycosidic monomers that were readily prepared by one‐pot method without any protection of the hydroxy groups on the starting free saccharides. The glycomonomers were synthesized by the direct synthesis of thioglycosides using 2‐chloro‐1,3‐dimethylimidazolinium chloride and 4‐aminobenzentiol, and the following acrylamidation. They were co‐polymerized with acrylamide into glycopolymers by reversible addition‐fragmentation chain transfer polymerization using a trithiocarbonate derivative as a chain transfer agent. The gold nanoparticles and gold‐coated quartz crystal microbalance sensor immobilized with the thiol‐terminated glycopolymers exhibited high affinity for the corresponding lectins due to multivalent interaction between saccharides and protein in aqueous solution. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 3513–3520     

One‐pot synthesis of polyfluoroterphenyls via palladium‐catalyzed Suzuki–Miyaura coupling of chlorobromobenzene and CH bond functionalization of perfluoroarenes

An efficient tandem route for the synthesis of polyfluoroterphenyl derivatives has been developed. The target compounds were obtained in moderate to good yields by a Pd(OAc)₂‐catalyzed three‐component coupling reaction involving palladium‐catalyzed direct C? H activation of perfluoroarenes. This in turn will set the stage for a wide application of this useful reaction for the synthesis of fluorinated liquid crystal compounds containing the privileged polyfluoroterphenyl structure. Copyright © 2014 John Wiley & Sons, Ltd.     

Precisely controlled copper(0)‐catalyzed one‐pot reaction: Concurrent living radical polymerization and click chemistry

Copper(0)‐catalyzed one‐pot reaction combining living radical polymerization and “click chemistry” was investigated. By precisely tuning reaction time, three novel well‐defined polymers with different degree of carboxyl substitution, poly(propargyl methacrylate) (PPgMA), poly(1‐(4‐carboxyphenyl)‐[1,2,3]triazol‐4‐methyl methacrylate) (PCTMMA), and poly(1‐(4‐carboxyphenyl)‐[1,2,3]triazol‐4‐methyl methacrylate‐co‐propargyl methacrylate) (PCTMMA‐co‐PPgMA) were selectively obtained via Cu(0) powder/N,N,N′,N″,N″‐pentamethyldiethylenetriamine (PMDETA) cocatalyzed LRP and click chemistry. In addition, gel permeation chromatography and ¹H NMR analysis in conjunction with FTIR spectroscopy elucidate that one‐pot process undergoes three steps due to a pronounced rate enhancement of click reaction: (1) generating new monomer, 1‐(4‐carboxyphenyl)‐[1,2,3]triazol‐4‐methyl methacrylate (CTMMA); (2) copolymerization of two monomers (CTMMA and PgMA); (3) building homopolymer PCTMMA. Surprisingly, in contrast to typical Cu(I)‐catalyzed atom transfer radical polymerization (ATRP), copper(0)‐catalyzed one‐pot reaction showed high carboxylic acid group tolerance. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012     

Introduction of Ag/CuO/MCM‐48 as an efficient catalyst for the one‐pot synthesis of novel pyran‐pyrrole hybrids

Bimetallic silver and copper incorporated mesoporous MCM‐48 (Ag/CuO/MCM‐48) was synthesized by simple wet‐impregnation method. The knowledge about its structural properties was gathered by means of Fourier transform‐infrared, energy‐dispersive X‐ray, X‐ray diffraction, field emission‐scanning electron microscopy, transmission electron microscopy and Brunauer–Emmett–Teller analyses. The catalytic activity of Ag/CuO/MCM‐48 was examined in the one‐pot three‐component reaction of 3‐(1‐methyl‐1H‐pyrrol‐2‐yl)‐3‐oxopropanenitrile, malononitrile and various aromatic aldehydes leading to novel pyran‐pyrrole hybrid derivatives in reduced reaction times (5–10 min) and excellent yields (88–97%). Application of Ag/CuO/MCM‐48 as a potent heterogeneous catalyst with good reusability up to five times, use of ethanol as an eco‐compatible medium and chromatography‐free work‐up are some crucial green aspects of this procedure.     

One‐pot synthesis of 3,4‐dihydropyridin‐2‐ones via tandem reaction of Blaise reaction intermediate and acrylic ester

An efficient method for the synthesis 3,4‐dihydropyridin‐2‐ones has been developed via tandem one‐pot Michael‐type addition and cyclization of the Blaise reaction intermediate and acrylic ester. A series of readily available nitriles, bromoacetic esters and acrylic esters have been employed to examine the scope of substrates for this method. Copyright © 2015 John Wiley & Sons, Ltd.     

1‐(α‐Aminobenzyl)‐2‐naphthol as phosphine‐free ligand for Pd‐catalyzed Suzuki and one‐pot Wittig‐Suzuki reaction

Air stable and easily accessible, 1‐(α‐aminobenzyl)‐2‐naphthols are used as efficient phosphine‐free ligands in palladium‐catalyzed Suzuki reaction for a variety of substrates under conventional heating as well as ultrasonic conditions. Multi‐brominated aromatic substrates were successfully converted to corresponding arylated moieties with good conversion and selectivity. A novel one‐pot two‐step cascade reaction strategy involving Wittig and Suzuki reactions is developed for efficient synthesis of 4‐styryl biphenyls (C₆‐C₂‐C₆‐C₆ unit). Copyright © 2012 John Wiley & Sons, Ltd.     

Application of Cu(Hdmg)2 as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

In this article, we have developed a novel and simple one‐pot reductive acetylation of aromatic nitro compounds with sodium borohydride (NaBH₄) in ethyl acetate (EtOAc) under reflux conditions in the presence of the bis(dimethylglyoximato)copper(II) complex [Cu(Hdmg)₂] as an efficient and cost‐effective copper‐containing catalyst. Notably, using the above‐mentioned one‐pot reaction, the corresponding acetamide derivatives were obtained in high to excellent yields.     

Diastereoselective Synthesis of Functionalized Tetrahydropyrimidin‐2‐thiones via ZnCl2 Promoted One‐pot Reactions

In the presence of zinc chloride, the in situ generated β‐enamino ester from the reaction of morpholine, piperidine and pyrrolidine with methyl propiolate reacted, with aromatic aldehydes and thiourea in ethanol resulting in the functionalized tetrahydropyrimidin‐2‐thiones in satisfactory yields and with good diastereoselectivity. When aromatic aldehydes bearing electron‐withdrawing group were used in the reaction, the 4‐hydroxytetrahydropyrimidin‐2‐thione derivatives were obtained as the main product.