Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• most profound influence [10][11][12]. Regarding the development of new synthetic methodologies for the preparation of such molecules, these can be divided in two main categories: fluorination reactions [13][14][15][16] and the use of fluorinated building blocks [17]. The difference between them is that

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

• Soundararajan Karthikeyan,
• Radha Krishnan Shobana,
• Kamarajapurathu Raju Subimol,
• J. Helen Ratna Monica and
• Ayyanoth Karthik Krishna Kumar

Beilstein J. Org. Chem. 2020, 16, 1579–1587, doi:10.3762/bjoc.16.130

• for the synthesis of 3-(bromomethyl)coumarins. Literature-reported cycloaddition reactions of MBH acetates involving azides and alkynes [24][25][26][27][28]. Synthetic methodologies for triazolations of MBH adducts. a) Literature-reported indirect triazolation of MBH adducts [32][33]. b) This work

Copper-based fluorinated reagents for the synthesis of CF₂R-containing molecules (R ≠ F)

• Louise Ruyet and
• Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

• molecules using copper-based fluorinated reagents will be given. Keywords: copper; difluoromethylation; fluorinated reagents; fluorine chemistry; synthetic methodologies; Introduction In a society in which fluorinated molecules are playing a pivotal role in pharmaceutical and agrochemical industries as

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• such as tetrakis(pentafluorophenyl)porphyrin (TPFPP) is more efficient in an oxidative quenching compared to an electron-rich (e.g., TPP) remained to be elucidated. In this regard, our research group has contributed in the last 10 years with new porphyrin/chlorin synthetic methodologies, and

Efficient method for propargylation of aldehydes promoted by allenylboron compounds under microwave irradiation

• Jucleiton J. R. Freitas,
• Queila P. S. B. Freitas,
• Silvia R. C. P. Andrade,
• Juliano C. R. Freitas,
• Roberta A. Oliveira and
• Paulo H. Menezes

Beilstein J. Org. Chem. 2020, 16, 168–174, doi:10.3762/bjoc.16.19

• great care on a case-by-case basis. Even so, the search for safer alternatives to current synthetic methodologies avoiding the use of moisture/air-sensitive organometallics and, more important, the development of solvent-free protocols are in accordance with the concept of environmental impact factor (E

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• conditions through covalent approaches. By using common synthetic methodologies chemists are able to proficiently synthesize a variety of both natural and unnatural molecular scaffolds [4][5][6]. The era of supramolecular chemistry began with the introduction of coordination theory by Alfred Werner in 1893

Synthesis of nonracemic hydroxyglutamic acids

• Dorota G. Piotrowska,
• Iwona E. Głowacka,
• Andrzej E. Wróblewski and
• Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

• ) also appeared attractive providing two or three predefined stereogenic centers. In more sophisticated approaches application of chiral auxiliaries allowed to generate vicinal or 1,3-aminoalcohol units of the required stereochemistries. Currently available synthetic methodologies towards hydroxyglutamic

• discussed which allow, for example, to differentiate between α and ω carboxy groups. Although syntheses of particular enantiomers of hydroxyglutamic acids look to be optimal, e.g., (2S,4S)-3 or (2S,4R)-3 via hydroxylation of the protected glutamic or pyroglutamic acids, synthetic methodologies to the other

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

• Paris E. Georghiou,
• Shofiur Rahman,
• Abdullah Alodhayb,
• Hidetaka Nishimura,
• Jaehyun Lee,
• Atsushi Wakamiya and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2018, 14, 2488–2494, doi:10.3762/bjoc.14.225

• result of Gutsche’s synthetic methodologies many researchers have been able to employ these calix[n]arenes and modified derivatives thereof in a great variety of ingenious applications. These applications have included a myriad of synthetic modifications to both, or either, of their upper and lower rims

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• much milder route to these heterocycles than traditional synthetic methodologies, which typically use harsh conditions. Semicarbazones are readily synthesised from the corresponding aldehydes, so these starting materials are easily accessible. The yields are very good to excellent (86–96%), while the

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

• Kartik Temburnikar and
• Katherine L. Seley-Radtke

Beilstein J. Org. Chem. 2018, 14, 772–785, doi:10.3762/bjoc.14.65

• ]. Pseudouridine is a naturally occurring C-nucleoside that was first discovered in the 1950s [45][46][47][50]. Subsequently, many more C-nucleosides were discovered and their medicinal properties evaluated (Figure 4) [18][29][37][45][46][47][48][49][50][60][61][62]. Due to advances in synthetic methodologies over

Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

• Prajwalita Das,
• Etsuko Tokunaga,
• Hidehiko Akiyama,
• Hiroki Doi,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

• structures of various pharmaceuticals, agrochemicals and coatings contain fluorine or fluorinated functional groups [4][5][6][7][8][9]. Therefore, the development of efficient synthetic methodologies for organofluorine compounds has gained much attention [10][11][12][13][14][15]. Our research group has been

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

• Imane Nekkaa,
• Márta Palkó,
• István M. Mándity and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

• addition, they are present in several natural frameworks [42][43][44]. We wanted to exploit the benefits of flow processing for reaction optimization and synthesis and develop novel sustainable synthetic methodologies with possible useful applications for the pharmaceutical industry. Our results show that

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

• availability of homogeneous structurally distinct lipid A, the development of divergent and reproducible approaches for the synthesis of various types of lipid A has become a subject of considerable importance. This review focuses on recent advances in synthetic methodologies toward LPS substructures

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• . Improvement in new synthetic methodologies under mechanomilling conditions with better results are always demanding, rather than “greening” the solution phase synthesis. Mechanochemical aldol condensation reactions [48]. Enantioselective organocatalyzed aldol reactions under mechanomilling. a) Based on binam

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

• Carolina S. García,
• Paula M. Uberman and
• Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

• an economic and environmental standpoint, it is highly desirable to develop more environmentally friendly synthetic methodologies. Several studies were dedicated to the design of a novel catalytic system, that are more accessible, robust, efficient and ligand-free [19]. In that sense, nanoparticles

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

• Işıl Yenice,
• Sinan Basceken and
• Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

• synthetic method for the construction of the pyrrolopyrazinone core structure as well as for its derivatives is not described in the literature [14]. Recently, we developed new synthetic methodologies for the synthesis of various pyrrole-fused new heterocycles using alkyne cyclization reactions [15][16][17

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• wide range of in vivo applications, which has been the topic of several recent reviews [13][14][15]. Following the serendipitous discovery by Xu et al. during the separation and purification of single-walled carbon nanotubes (SWCNTs) [16], the development of synthetic methodologies to access these

Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

• Masahiro Torii,
• Kohsuke Kato,
• Daisuke Uraguchi and
• Takashi Ooi

Beilstein J. Org. Chem. 2016, 12, 2099–2103, doi:10.3762/bjoc.12.199

• important class of biologically relevant molecules, and numerous efforts have been made for the development of reliable synthetic methodologies to enable the installation of the C-3 stereogenic center [1][2][3][4]. Among them, the direct stereoselective functionalization of 3-monosubstituted oxindoles is a

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• ], substrate recognition [29] and/or biological systems [30][31]. Among the synthetic methodologies to access to pNHC metal complexes [32][33][34][35][36][37][38][39][40], recently N-arylimine functionalized pNHC iridium complexes were obtained using excess of [Ir(cod)(µ-Cl)]2 [41], and next deprotonation of

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• limitations in existing synthetic methodologies, particularly in the direct preparation of N-substituted amino derivatives. 2-Aminothiophenes have traditionally been synthesized from mercapto- or halogen-substituted thiophenes through nucleophilic displacements [19]. More recently, these derivatives have been

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• the regioselective ring opening of 1,2-cyclopropanated carbohydrates and the radical addition reaction of glycals [11][12][13][14][15]. Although the synthetic methodologies developed for the synthesis of C-glycosides and 2-C-branched sugars are extensively studied, the synthesis of 1,2-cis-2-C

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• possibilities and challenges of implementing other synthetic methodologies. In view of potential industrial application, the choice of reactor setup, electrode type and reaction pathway has a large influence on the sustainability and efficiency of the process. Keywords: carbon dioxide; carboxylic acids

Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools

• Luciana Baldoni and
• Carla Marino

Beilstein J. Org. Chem. 2014, 10, 1651–1656, doi:10.3762/bjoc.10.172

• complex products and bioactive compounds. Among the glycosans, the anhydro sugars involving the anomeric center in the ring formation, the 1,6-anhydro sugars are the most common and useful building blocks [1][2]. They can play a role in synthetic methodologies aiming at the obtainment of regioselectively

Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis

• Jingran Tao,
• Li-Mei Jin and
• X. Peter Zhang

Beilstein J. Org. Chem. 2014, 10, 1282–1289, doi:10.3762/bjoc.10.129

• efforts have been made for the construction of this class of nitrogen-containing three-membered ring compounds [3][4][5][6][7][8]. Among synthetic methodologies, catalytic aziridination of alkenes with nitrene sources via “C2 + N1” addition has received the most attention because of the abundance of both

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

• . As the fine chemicals and pharmaceutical industries are eventually adopting green chemistry synthetic methodologies [13], this method provides both industries with a clean route to valued compounds that are widely used in many industrial sectors. Chemical structure of SiliaCat DPP-Pd. Heterogeneously