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

Recent advances in materials for organic light emitting diodes

• Eli Zysman-Colman

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

• Organic Chemistry covers novel phosphorescent and TADF materials design and their inclusion as emitters in OLEDs. Some highlights in this issue include the work of Thanh-Tuân Bui et al., who provide a welcome perspective on blue TADF materials for OLEDs in the form of a review article [2]. Cristina

A pyridinium/anilinium [2]catenane that operates as an acid–base driven optical switch

• Sarah J. Vella and
• Stephen J. Loeb

Beilstein J. Org. Chem. 2018, 14, 1908–1916, doi:10.3762/bjoc.14.165

• derivatize, [2]rotaxanes are deemed easier to fine-tune from a structural perspective than [2]catenanes. Although we were able to create an optically sensitive [2]catenane molecular shuttle with the bis(pyridinium)ethane and benzylanilinium recognition motifs, we could not achieve the true ON/OFF, bistable

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• performed using 118a–e as catalysts and isopropanol as a secondary alcohol hydride donor (Scheme 38). Although 99% ee was achieved with catalyst 118a in initial conversion stage, from the perspective of yield and enantioselectivity VANOL-derived phosphite catalyst 118d which has an extended π-delocalization

Oligonucleotide analogues with cationic backbone linkages

• Melissa Meng and
• Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

• systems, vide supra) as the stereoselective synthesis of stereogenic phosphate derivatives is challenging. Therefore, achiral artificial linkages such as guanidinium groups may be considered advantageous from a stereochemical perspective. For the first synthesis of a pentameric thymidinyl DNG in 1996

Stereoselective nucleophilic addition reactions to cyclic N-acyliminium ions using the indirect cation pool method: Elucidation of stereoselectivity by spectroscopic conformational analysis and DFT calculations

• Koichi Mitsudo,
• Junya Yamamoto,
• Tomoya Akagi,
• Atsuhiro Yamashita,
• Masahiro Haisa,
• Kazuki Yoshioka,
• Hiroki Mandai,
• Koji Ueoka,
• Christian Hempel,
• Jun-ichi Yoshida and
• Seiji Suga

Beilstein J. Org. Chem. 2018, 14, 1192–1202, doi:10.3762/bjoc.14.100

• physiological and pharmacological activities [1][2][3]. As many of these compounds feature asymmetric carbon atoms at the α-position of the cyclic amine, the stereoselective carbon–carbon bond formation at this position is of great importance from the perspective of drug discovery [4][5]. Meanwhile the “cation

Are dispersion corrections accurate outside equilibrium? A case study on benzene

• Tim Gould,
• Erin R. Johnson and
• Sherif Abdulkader Tawfik

Beilstein J. Org. Chem. 2018, 14, 1181–1191, doi:10.3762/bjoc.14.99

• forces Dispersion forces are a semi-classical effect coming from quantum fluctuations. Most simply, they can be viewed from the perspective of pairs of interacting fluctuating dipoles, in which a temporary dipole in one (sub)system induces a dipole in the other, and consequently lowers the total energy

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• Strecker-type reaction could be effected in a ball mill using catalytic anhydrous ferricyanide in the presence of silica [114]. From a theoretical perspective, Hansma proposed that such mechanical energy could be supplied within moving mica sheets under high molecular crowding conditions [115]. In contrast

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• . The general architecture of PDCs consists of three building blocks: the tumor-homing peptide, the cytotoxic agent and the biodegradable connecting linker. The aim of the current review is to provide a spherical perspective on the basic principles governing PDCs, as also the methodology to construct

• Table 2. Representative examples of PDCs targeting cancer cells Integrating the basic design principles in PDCs pinpointed above, a list of representative developed examples is analyzed below, so as to provide a spherical perspective regarding peptide–drug conjugation chemistry. Currently, there are two

Phosphodiester models for cleavage of nucleic acids

• Satu Mikkola,
• Tuomas Lönnberg and
• Harri Lönnberg

Beilstein J. Org. Chem. 2018, 14, 803–837, doi:10.3762/bjoc.14.68

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

• Longcheng Hong,
• Sebastian Ahles,
• Andreas H. Heindl,
• Gastelle Tiétcha,
• Andrey Petrov,
• Zhenpin Lu,
• Christian Logemann and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48

• attributed to the free vacant p-orbital of the boron atom leading to further transformations, such as decomposition via radicals (O2), reactions with nucleophiles (H2O) as well as the formations of adducts. From this perspective, a suitable Lewis base may form a Lewis complex and subsequently occupy the p

Mechanochemistry

• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 2372–2373, doi:10.3762/bjoc.13.234

• otherwise impossible chemical reactivity in many cases. From a green chemistry perspective, mechanochemical activation conducted by milling, shearing, pulling or ultrasonic irradiation allows for the possibility to drastically reduce the amount of solvent needed during chemical reactions, even to the point

Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

• Yaroslav D. Boyko,
• Valentin S. Dorokhov,
• Alexey Yu. Sukhorukov and
• Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

• nucleophile as well as asymmetric catalysis still remains to be studied in these reactions. The high efficiency and stereoselectivity of the enolate addition to nitrosoalkenes make this strategy perspective for application in total synthesis that has been recognized since 1970s. Thus, Oppolzer and co-workers

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• seems to have wide applicability…” and disclosed their attempts to link the reaction counterparts with dicarboxylic acids. This served as an ultimate perspective on future developments in the field, but about a decade had passed before Ziegler resurrected this concept. Flexible succinoyl and related

A recursive microfluidic platform to explore the emergence of chemical evolution

• David Doran,
• Marc Rodriguez-Garcia,
• Rebecca Turk-MacLeod,
• Geoffrey J. T. Cooper and
• Leroy Cronin

Beilstein J. Org. Chem. 2017, 13, 1702–1709, doi:10.3762/bjoc.13.164

• way towards answering the latter question. This approach engenders a “chemically agnostic” perspective, in which strict adherence to the chemical repertoire found in currently extant biochemistry is not required [9]. Indeed, the simplest biological units can be considered as nothing more than complex

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• membrane components. Furthermore, experimental conditions are sometimes implausible from the geochemical perspective. Finally, the evolutionary continuity of the systems, which should be paramount to explain the emergence of protocellular systems and evolution towards true cells, is often neglected in

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

• Alexei N. Kiselev,
• Olga K. Grigorova,
• Alexei D. Averin,
• Sergei A. Syrbu,
• Oskar I. Koifman and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

• application of such medicaments are antitumor remedies and non-invasive diagnostic imaging agents for PET, SPECT and MRI methods [5]. The combination of porphyrin and heterocyclic moieties in one molecule is perspective for the design of new compounds with potential powerful pharmaceutical properties. Up to

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• dissipative self-assembling structures, creating new forms of smart materials [31][32][33][34][35]. Yet, we are severely limited by too few examples of systems which are both extensive enough to exhibit dynamics, and at the same time, simple enough to be tunable [36]. In this perspective, we will attempt to

• perspective, however, urges an approach using a synthetic strategy based on the stepwise build-up of complex molecular systems. We envision the development of a toolbox that allows us to go beyond describing and understanding systems, extending to the rational design of function arising from a collection of

• “synthetic moves” We hope that the method developed here allows researchers, and especially chemists, to address important features of self-organization in complex systems. We briefly showed how the tuning of molecular structures allows one to explore the robustness of CRNs. From this perspective, other

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• reaction with homophthalic anhydride (HPA). The compounds obtained contain a benzene-fused, privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline core and are distinctly encumbered from steric perspective. The novel compounds have been characterized by NMR spectroscopy, high-resolution mass

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• -dihydroindolo[3,2-b]carbazole (indolo[3,2-b]carbazole, ICZ) has been successfully used as a basic structural fragment of perspective electroluminescent, hole-transporting materials and light-harvesting dyes for organic light emitting diodes (OLEDs) [7][8][9][10][11][12][13], organic field-effect transistors

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• simplifying assumptions, both in terms of the molecular and the organisational features of life as we currently know them. The simplifications tried so far have met with limited success, probably because they represent oversimplifications. From a historical perspective, one can say that the extraordinary

• transitions like the one portrayed in Figure 1, looking at it from an evolutionary perspective, is that the individuals that lead the process are protocellular systems whose phenotypic space is intrinsically wider than that associated to replicating molecular entities (as in traditional approaches to the

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• application to chemistry, particularly synthetic chemistry, is still at an embryonic stage but they have the potential to generate rapid paradigm changes in the short to medium term. This perspective paper provides a brief overview of these methods for chemists who may wish to understand their current and

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• efforts on the development of a post-GBB transformation strategy for the concise synthesis of diverse imidazo[1,2-a]pyridine-fused isoquinoline systems. Results and Discussion From a design perspective, we envisioned that the imidazo[1,2-a]pyridine-fused isoquinoline 6a [49][50] could be constructed

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

• reviews [77][78]. Here we describe very recent reports with the aim to highlight the potential of flow chemistry in the field of hazardous chemistry under a greener perspective. Diazo compounds are recognized as versatile reagents in organic synthesis. Nevertheless, diazo compounds are also considered

Dimerization reactions of aryl selenophen-2-yl-substituted thiocarbonyl S-methanides as diradical processes: a computational study

• Michael L. McKee,
• Grzegorz Mlostoń,
• Katarzyna Urbaniak and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 410–416, doi:10.3762/bjoc.13.44

• electronegative nature of Se in the five-membered ring increases the spin density on the adjacent C(2) atom. Therefore, from the perspective of spin density, the formation of the six-membered ring 13 should be preferred. With respect to the most stable conformer 12E, the free energy barrier of the reaction