Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

Asymmetric synthesis of CF₂-functionalized aziridines by combined strong Brønsted acid catalysis

• Xing-Fa Tan,
• Fa-Guang Zhang and
• Jun-An Ma

Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60

• . Scale-up experiment to 4a and further synthetic transformations. Representative screening results of the asymmetric aziridination reaction of PhSO2CF2CHN2.a Supporting Information Supporting Information File 244: Experimental procedures, compound characterization, NMR spectra of all new compounds, and

Copper-catalyzed O-alkenylation of phosphonates

• Nuria Vázquez-Galiñanes,
• Mariña Andón-Rodríguez,
• Patricia Gómez-Roibás and
• Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56

• has allowed to perform a wide range of previously unknown synthetic transformations [19][20][21][22][23][24][25][26][27][28][29]. In these reactions, aryl(vinyl)Cu(III) species [30][31] have been proposed as key intermediates to undergo reactions with a variety of nucleophiles. Fañanás-Mastral and

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• undergoing synthetic transformations regio- and enantioselectively (Figure 5) [53][54]. With the aid of photoredox catalysis, the active radical moieties can easily undergo nonclassical nucleophilic direct coupling reactions. Also, there is a possibility of intermediate catalytic moiety excitation via

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

• Qiao Li,
• Chen Zhuang,
• Donghua Wang,
• Wei Zhang,
• Rongxuan Jia,
• Fengxia Sun,
• Yilin Zhang and
• Yunfei Du

Beilstein J. Org. Chem. 2019, 15, 2958–2965, doi:10.3762/bjoc.15.291

• reagents have emerged as a class of efficient and environmentally benign nonmetal “green” oxidants [66][67][68][69][70][71][72][73]. For instance, iodosobenzene (PhIO) [74] has been widely used in many synthetic transformations. It was found that PhIO is efficient in realizing epoxidation of olefins [75

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• pathways for synthetic transformations that are otherwise quite challenging. Not only the environmental advantages with respect to substituting toxic chemical reagents with mass-free electrons and minimizing the reagent waste generated, but also in terms of shortening of tedious multistep reaction

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• properties, synthetic transformations, organometallic chemistry and metal-catalysed reactions, an excellent review was recently published by Radhakrishnan and co-workers [33]. This highlight article is intended to give the reader an overview of the varied and exceptional cycloaddition chemistry of fulvenes

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

• Hamada S. A. Mandour,
• Yoko Nakagawa,
• Masaya Tone,
• Hayato Inoue,
• Nansalmaa Otog,
• Ikuhide Fujisawa,
• Soda Chanthamath and
• Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

• the catalyst leakage during the work-up. Synthetic transformations of 2d and 2f In order to demonstrate the advantages of products, further synthetic transformations of the cyclopropane products were investigated. A ring opening and direct amidation of the chiral cyclopropane-fused γ-lacton 2d using

Microfluidic light-driven synthesis of tetracyclic molecular architectures

• Javier Mateos,
• Nicholas Meneghini,
• Marcella Bonchio,
• Nadia Marino,
• Tommaso Carofiglio,
• Xavier Companyó and
• Luca Dell’Amico

Beilstein J. Org. Chem. 2018, 14, 2418–2424, doi:10.3762/bjoc.14.219

• enabling novel light-driven synthetic transformations. Results and Discussion The reaction between 2-methylbenzophenone (1a) and coumarin (2a) was initially screened in a MFP of 1000 μL volume, using 1.5 equiv of 1a and a residence time of 26.6 min (Table 1 and Table S3 in the Supporting Information File 1

• chromatographic purification. Noteworthy, compounds 6a–9a embody different functionalities suitable for additional synthetic transformations. Conclusion In conclusion we have developed an effective light-driven microfluidic method for the synthesis of valuable tetracyclic molecular architectures using

The mechanochemical synthesis of quinazolin-4(3H)-ones by controlling the reactivity of IBX

• Md Toufique Alam,
• Saikat Maiti and
• Prasenjit Mal

Beilstein J. Org. Chem. 2018, 14, 2396–2403, doi:10.3762/bjoc.14.216

• stability, controlled oxidizing ability, and environmentally benign nature make them highly suitable for the development of new synthetic transformations [13][14][15][16][17]. The chemistry of iodine(V) reagents has been well documented in a number of reviews [18][19][20]. In continuation of our research

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

• Xiang Li,
• Pinhong Chen and
• Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

• the overlap of the 5p orbital of iodine atom with the orbitals of two ligands (Figure 1) [9]. The chemistry of hypervalent iodine(III) reagents is now a well-established area in organic chemistry. They are efficient oxidants in many synthetic transformations, such as oxidation of alcohols and phenols

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• 59 paved the way for the synthesis of protected heparin pentasaccharide 48 (Scheme 11d). Preactivation-based chemoselective glycosylation of thioglycosides Thioglycosides are one of the most commonly utilized building blocks due to their high stabilities under a wide range of synthetic

• transformations commonly encountered in building block preparation [41]. At the same time, mild promoters are available for thioglycoside activation. The anomeric reactivities of thioglycosides towards glycosylation can be significantly influenced by the protective groups on the glycan ring as well as the size

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

• Andrea Porcheddu,
• Evelina Colacino,
• Giancarlo Cravotto,
• Francesco Delogu and
• Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

• available for a variety of synthetic transformations [1]. The reason for this lies in the capability of the carbonyl group to generate other possible functional groups through more or less complex chemical transformations [2]. The ubiquity of the carbonyl group in biomolecules adds further value to its

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

• Joseph L. Howard,
• William Nicholson,
• Yerbol Sagatov and
• Duncan L. Browne

Beilstein J. Org. Chem. 2017, 13, 1950–1956, doi:10.3762/bjoc.13.189

• significant number of mechanochemical synthetic transformations reported [3][4][5][6]. However, for the synthetic community, perhaps the most interesting examples of mechanochemical reactions are not those that are merely solventless but those in which different reactivity or selectivity arises, as well as

Characterization of non-heme iron aliphatic halogenase WelO5* from Hapalosiphon welwitschii IC-52-3: Identification of a minimal protein sequence motif that confers enzymatic chlorination specificity in the biosynthesis of welwitindolelinones

• Qin Zhu and
• Xinyu Liu

Beilstein J. Org. Chem. 2017, 13, 1168–1173, doi:10.3762/bjoc.13.115

• molecules, synthetic transformations that allow for the selective modification of this type of functional group have been long sought after. While numerous methods have emerged that permit the late-stage functionalizations of inert aliphatic carbons with oxygen-containing functionalities [5][6][7][8

DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support

• Johnny N. Naoum,
• Koushik Chandra,
• Dorit Shemesh,
• R. Benny Gerber,
• Chaim Gilon and
• Mattan Hurevich

Beilstein J. Org. Chem. 2017, 13, 806–816, doi:10.3762/bjoc.13.81

• . DMAP plays a wide catalytic role in various synthetic transformations, e.g., acylations, alkylations, silylations, esterifications, and many others, as it acts as nucleophile rather than a base [33][34][35][36][37][38][39][40]. Compared to DMAP, pyridine is a weak nucleophile as it does not have any

Investigation on the reactivity of α-azidochalcones with carboxylic acids: Formation of α-amido-1,3-diketones and highly substituted 2-(trifluoromethyl)oxazoles

• Kandasamy Rajaguru,
• Arumugam Mariappan,
• Rajendran Suresh,
• Periasamy Manivannan and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2015, 11, 2021–2028, doi:10.3762/bjoc.11.219

• reactive intermediate in several synthetic transformations [10][11][12][13][14][15]. The chemistry of 2H-azirines has been extensively explored because of its strained molecular structure, unique reactivity and synthetic applications [10][11][12][13][14][15][16][17][18][19][20][21][22]. α-Substituted 2H

Hybrid macrocycle formation and spiro annulation on cis-syn-cis-tricyclo[6.3.0.0^2,6]undeca-3,11-dione and its congeners via ring-closing metathesis

• Sambasivarao Kotha,
• Ajay Kumar Chinnam and
• Rashid Ali

Beilstein J. Org. Chem. 2015, 11, 1123–1128, doi:10.3762/bjoc.11.126

• hydrogenation steps (Scheme 1). A variety of synthetic transformations involving tricyclic diones 5 and 2 were reported in the literature [47]. To expand the utility of building block 2 in organic synthesis, we conceived a simple retrosynthetic approach to macrocylic aza-polyquinane 6 and spiro-polyquinane

Morita–Baylis–Hillman reaction of acrylamide with isatin derivatives

• Radhey M. Singh,
• Kishor Chandra Bharadwaj and
• Dharmendra Kumar Tiwari

Beilstein J. Org. Chem. 2014, 10, 2975–2980, doi:10.3762/bjoc.10.315

• called MBH adducts. These are versatile synthons as they constitute several functionalities within close proximity, which aids in further synthetic transformations. Thus, as expected, the reaction has emerged as a powerful synthetic tool. It has seen exponential growth in several directions involving not

Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates

• Jan Szabo,
• Kerstin Karger,
• Nicolas Bucher and
• Gerhard Maas

Beilstein J. Org. Chem. 2014, 10, 2255–2262, doi:10.3762/bjoc.10.234

• (benzylamino)guanidinium chloride and aryl isothiocyanates. Here, a cyclization reaction occurred after thiocarbamoylation of the first NH2 group. The diverse reaction routes reported in this paper nicely demonstrate the versatility of TAG-derived 1,2,3-tris(alkylamino)guanidinium ions respect to synthetic

• transformations using heterocumulenes as reagents. Due to their particular molecular shape and the presence of hydrogen-bond donor and acceptor groups, the obtained 1,2,3-tris(ureido)guanidinium salts 7 and the derived neutral guanidine 8 may become of interest as host components in host–guest complexes, for

Application of cyclic phosphonamide reagents in the total synthesis of natural products and biologically active molecules

• Thilo Focken and
• Stephen Hanessian

Beilstein J. Org. Chem. 2014, 10, 1848–1877, doi:10.3762/bjoc.10.195

• synthetic transformations [1]. This chiral phosphonamide typically yields reaction products with excellent stereocontrol, which are easily isolated as diastereometrically pure or highly enriched compounds. Many are crystalline solids that can be purified further by recrystallization. Diazaphosphorinane 3

Visible-light photoredox catalysis enabled bromination of phenols and alkenes

• Yating Zhao,
• Zhe Li,
• Chao Yang,
• Run Lin and
• Wujiong Xia

Beilstein J. Org. Chem. 2014, 10, 622–627, doi:10.3762/bjoc.10.53

• others [32][33][34][35][36][37][38][39][40][41][42][43][44] demonstrated the usefulness of Ru(bpy)3Cl2 and its application to various visible-light-induced synthetic transformations, visible-light-photoredox catalysis has emerged as a growing field in organic chemistry and has been successfully applied

One-pot synthesis of cyanohydrin derivatives from alkyl bromides via incorporation of two one-carbon components by consecutive radical/ionic reactions

• Shuhei Sumino,
• Akira Fusano,
• Hiroyuki Okai,
• Takahide Fukuyama and
• Ilhyong Ryu

Beilstein J. Org. Chem. 2014, 10, 150–154, doi:10.3762/bjoc.10.12

• formylation. Thus, we thought that the two step radical/ionic reactions can be extended to the consecutive C–C bond forming reactions. Cyanohydrins are important subunits frequently found in biologically active compounds and are also versatile building blocks for further synthetic transformations [20][21

Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines

• Alexander Penger,
• Cortney N. von Hahmann,
• Alexander S. Filatov and
• John T. Welch

Beilstein J. Org. Chem. 2013, 9, 2675–2680, doi:10.3762/bjoc.9.303

• stereochemistry. Optimization of β-lactam synthesis will require a better understanding of the nature of the competing, undesirable reactions and enable utilization of this unique construct in further synthetic transformations. The product β-lactams are a useful entrée to the diastereoselective synthesis of