A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• ambient temperature for 12 h under a hydrogen atmosphere. Finally, the Pd–Cu/C catalyst was collected by filtration, washed with methanol, and dried. An efficient one-pot sequential Sonogashira-“click” reaction toward heterocyclic structures was disclosed using the same catalyst. In this regard

DABCO- and DBU-promoted one-pot reaction of N-sulfonyl ketimines with Morita–Baylis–Hillman carbonates: a sequential approach to (2-hydroxyaryl)nicotinate derivatives

• Soumitra Guin,
• Raman Gupta,
• Debashis Majee and
• Sampak Samanta

Beilstein J. Org. Chem. 2018, 14, 2771–2778, doi:10.3762/bjoc.14.254

• ketimines; one-pot sequential; pyridines; Introduction Substituted pyridines are one of the most fascinating classes of heterocyclic molecules which are present in many biologically active natural and synthetic products [1][2][3]. In addition, several pyridine scaffolds have been used in agro-chemical

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

• Takashi Go,
• Akane Morimatsu,
• Hiroaki Wasada,
• Genzoh Tanabe,
• Osamu Muraoka,
• Yoshiharu Sawada and
• Mitsuhiro Yoshimatsu

Beilstein J. Org. Chem. 2018, 14, 2722–2729, doi:10.3762/bjoc.14.250

• compounds operate by inhibiting proteins or enzymes that regulate cell cycles, including cyclin-dependent kinases [9], tyrosine kinase [10], glycogen-synthase kinase and mitochondrial malate dehydrogenase [11]. These interesting biological activities led us to develop one-pot sequential or cascade protocols

• under Pummerer reaction conditions of sulfoxides and the results are shown in Scheme 3. We first examined the following one-pot sequential reactions of the selenium analog: the mCPBA oxidation of N-allylpyrrolomethylselenide 6a, the following Pummerer reaction, and final treatment with TBAH. The

Synthetic avenues towards a tetrasaccharide related to Streptococcus pneumonia of serotype 6A

• Aritra Chaudhury,
• Mana Mohan Mukherjee and
• Rina Ghosh

Beilstein J. Org. Chem. 2018, 14, 1095–1102, doi:10.3762/bjoc.14.95

• followed by NIS were added. The reaction mixture was allowed to reach −10 °C before another 30 mol % of TMSOTf were added; TLC after 45 minutes showed complete consumption of the starting materials. Thus the targeted tetrasaccharide derivative was prepared via a three component, one-pot sequential

• ]. After this, the Demchenko group improved these early reports with a convergent approach using glycosyl thioimidates as complementary glycosyl donors with respect to thioglycosides [22][23][24][25]. Herein, we wish to report synthetic routes to the SPn 6A tetrasaccharide via stepwise as well as one-pot

• sequential glycosylation strategies. Results and Discussion Keeping in mind our objective to synthesize the SPn 6A tetrasaccharide following stepwise as well as one-pot synthetic strategies based on common building blocks, a retrosynthetic analysis was made which led us to galactose-based donor 2 [26

One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates

• Jun Ki Kim,
• Hwan Jung Lim,
• Kyung Chae Jeong and
• Seong Jun Park

Beilstein J. Org. Chem. 2018, 14, 243–252, doi:10.3762/bjoc.14.16

• those of others. Keywords: 5-(heterocyclic)thiophenes; one-pot sequential synthesis; sulfur ylide; tetrasubstituted thiophene; Introduction Since the discovery of stable sulfonium ylides 1 in 1930 [1] and the pioneering work of several research groups during the 1960s (2 and 3) [2][3][4][5][6][7][8][9

• -pot sequential synthesis of the trisubstituted 5-(pyridine-2-yl)thiophenes 8a. Substrate: amalonitrile; b5,5-dimethylcyclohexane-1,3-dione. The substitution reaction with MeOH. Examination of N,S-acetals substituted with a heterocycle (7aa–k) or an arene (7l–p). 1H NMR studies of Meldrum’s acid-based

• ], 4 [11][12], 5 [33][34], 6 [35][36][37][38]. Metal-free synthesis of thiophene-based heterocycles (A) [54][55], (B) [56]. X-ray crystal structures of 8ad and 8an [68]. The proposed structure of sulfur ylide-like intermediates; resonance contributors (mesomeric structures) [69][70][71][72][78]. One

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

• Gastón Silveira-Dorta,
• Sergio J. Álvarez-Méndez,
• Víctor S. Martín and
• José M. Padrón

Beilstein J. Org. Chem. 2016, 12, 957–962, doi:10.3762/bjoc.12.94

• aldehydes. It comprises the one-pot sequential reduction to aldehyde with DIBAL-H at −78 °C and subsequent in situ addition of Grignard reagents. Remarkably, our method is friendly with serine and threonine derivatives without the requisite to protect the β-hydroxy group. With this tool in hand, we thought

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• (PyrDipSi) [72][73] directing groups were proposed by the research group of Prof. V. Gevorgyan. The PyDipSi group was used for selective monoacetoxylation or pivaloyloxylation of the arene ortho-position [70][71], whereas the PyDipSi group allowed to achieve one-pot sequential acyloxylation of both ortho

A modular phosphate tether-mediated divergent strategy to complex polyols

• Paul R. Hanson,
• Susanthi Jayasinghe,
• Soma Maitra,
• Cornelius N. Ndi and
• Rambabu Chegondi

Beilstein J. Org. Chem. 2014, 10, 2332–2337, doi:10.3762/bjoc.10.242

• -mediated, one-pot, sequential RCM/CM/reduction process is reported. A modular, 3-component coupling strategy has been developed, in which, simple “order of addition” of a pair of olefinic-alcohol components to a pseudo-C2-symmetric phosphoryl chloride, coupled with the RCM/CM/reduction protocol, yields

• five polyol fragments. Each of the product polyols bears a central 1,3-anti-diol subunit with differential olefinic geometries at the periphery. Keywords: phosphate-tether; one-pot; sequential processes; organophosphorus; polyol; stereodivergent; Introduction 1,3-anti-Diol subunits are a central

• screening decks in early phase drug discovery. One aim of divergent synthetic strategies is to produce multiple scaffolds from a single set of starting materials [12]. In this regard, one-pot, sequential processes [13][14][15][16] are well suited to address this challenge by forming multiple bonds and

Efficient routes toward the synthesis of the D-rhamno-trisaccharide related to the A-band polysaccharide of Pseudomonas aeruginosa

• Aritra Chaudhury,
• Sajal K. Maity and
• Rina Ghosh

Beilstein J. Org. Chem. 2014, 10, 1488–1494, doi:10.3762/bjoc.10.153

• -rhamno-trisaccharide; deoxygenation on thioglycoside; multivalent glycosystems; one-pot sequential glycosylation; Pseudomonas aeruginosa; Introduction With the firm establishment of the critical roles played by oligosaccharides in diverse biological processes [1][2][3][4], the field of oligosaccharide

Clean and fast cross-coupling of aryl halides in one-pot

• Valerica Pandarus,
• Geneviève Gingras,
• François Béland,
• Rosaria Ciriminna and
• Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

• intermediate boronic acid pinacol ester. The overall process is described by Scheme 2. The SiliaCat DPP-Pd catalyst mediates the borylation and the subsequent Suzuki–Miyaura reaction in an elegant one-pot sequential synthesis. Hence, an aryl bromide is first converted into the boronic acid pinacol ester (step

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

• Samir Kundu,
• Babli Roy and
• Basudeb Basu

Beilstein J. Org. Chem. 2014, 10, 26–33, doi:10.3762/bjoc.10.5

• -dithioethers. Plausible mechanisms for the regioselective formation of vicinal and 1,3-dithioethers by using dry or moistened silica gel. Optimization of one-pot sequential substitution–hydrothiolation of allylic substrate with excess benzenethiol over silica at room temperature. Regioselective one-pot

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction

• Diego Carnaroglio,
• Katia Martina,
• Giovanni Palmisano,
• Andrea Penoni,
• Claudia Domini and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2013, 9, 2378–2386, doi:10.3762/bjoc.9.274

• a one-pot, sequential synthesis of urea derivatives from alkyl bromides. With the aim to verify the feasibility of the method under conventional heating, the protocol was tested in a Parr reactor (90 mL) for an easier scale-up. Results and Discussion The Staudinger–aza-Wittig reaction is extremely

• . Conclusion In conclusion, a MW-assisted, one-pot sequential protocol for the synthesis of urea derivatives from alkyl bromides has been described. This study has proven that in acetonitrile under high CO2 pressure the Staudinger–aza-Wittig reaction in presence of PS-PPh2 is strongly promoted. Excellent

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

• Jin-Sheng Yu,
• Feng Zhou,
• Yun-Lin Liu and
• Jian Zhou

Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157

• could be operated as a “one-pot” sequential reaction. After the reaction of 1i and 2 was run at 0 °C for five days a small amount of oxindole 1i still remained. Then, the reaction was warmed to room temperature, followed by the addition of Pd/C and ammonium formate. When TLC analysis revealed that the

Asymmetric one-pot sequential Friedel–Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme

• Kengo Akagawa,
• Ryota Umezawa and
• Kazuaki Kudo

Beilstein J. Org. Chem. 2012, 8, 1333–1337, doi:10.3762/bjoc.8.152

• Kengo Akagawa Ryota Umezawa Kazuaki Kudo Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan 10.3762/bjoc.8.152 Abstract In the presence of a peptide catalyst and the oxidative enzyme laccase, a one-pot sequential reaction including a Friedel

• with an α-oxygenation of aldehydes [24][25][26][27][28][29] in a one-pot sequential reaction. Meanwhile, our group has developed resin-supported peptide catalysts (Figure 2) for several organic reactions in aqueous media [30][31][32][33][34][35][36][37]. Since these catalysts can be applicable for the

• FCAA reaction toward α,β-unsaturated aldehydes through iminium intermediates [32][37], and an asymmetric α-oxyamination of aldehydes via enamines [33], they are expected to be suitable for a one-pot sequential reaction to make the chiral indoles mentioned above. Herein, we report on an enantioselective

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

• completion. A variety of amines were involved in this one-pot sequential three-component reaction allowing the introduction of different protecting groups of the indole moiety. This site-selective, Pd/Cu-catalyzed cross-coupling approach was also performed on 1-chloro-2-iodo-4-(trifluoromethyl)benzene as o

Gold-catalyzed propargylic substitutions: Scope and synthetic developments

• Olivier Debleds,
• Eric Gayon,
• Emmanuel Vrancken and
• Jean-Marc Campagne

Beilstein J. Org. Chem. 2011, 7, 866–877, doi:10.3762/bjoc.7.99

• an one-pot, sequential, reaction with first a gold(III)-catalyzed propargylic substitution followed by a gold(I)-catalyzed cycloisomerization, the bicyclic compound 37 was obtained in 71% yield [24][80][81][82]. Very recently, a remarkable one-pot reaction using an original gold(III) catalyst has

One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines

• Jonathan P. Brand,
• Clara Chevalley and
• Jérôme Waser

Beilstein J. Org. Chem. 2011, 7, 565–569, doi:10.3762/bjoc.7.65

• problem of reproducibility. Unfortunately, NaAuCl4 was not an efficient catalyst for the direct alkynylation of indole, as no reaction was observed when TIPS-EBX (1) was added to the reaction mixture. We then investigated the successive addition of NaAuCl4 and AuCl in the same pot. Interestingly, one-pot

• sequential processes using both Au(I) and Au(III) have not yet been reported. AuCl and TIPS-EBX (1) were added when full conversion of the NaAuCl4-catalyzed cyclization was observed. When 2 mol % of NaAuCl4 and 2 mol % AuCl were added, the second step was unsuccessful. However, with 2 mol % of NaAuCl4 and 4