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

Polyketide stereocontrol: a study in chemical biology

• Kira J. Weissman

Beilstein J. Org. Chem. 2017, 13, 348–371, doi:10.3762/bjoc.13.39

Catalytic Wittig and aza-Wittig reactions

• Zhiqi Lao and
• Patrick H. Toy

Beilstein J. Org. Chem. 2016, 12, 2577–2587, doi:10.3762/bjoc.12.253

• completed. However, will the research results summarized herein remain merely intellectual achievements or will they become commonly used synthetic methods in the future? Perhaps the answer to this question is how these new reaction systems are viewed from an environmental/green chemistry perspective. In

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• - and 6-membered monocyclic rings are most commonly made by [2 + 2 + 1] and [3 + 2 + 1] cycloadditions where 57% and 76% of them, respectively, have a 100% chance of being intrinsically green from a design perspective. A survey of over 2000 MCRs used to synthesize specific types of heterocyclic rings

• of ring construction strategy from a very different perspective that is rooted in an entirely different scientific field which also has enjoyed an even longer track record of research, namely combinatorics and enumeration. Specifically, we exploit the subject of integer partitioning [123][124][125

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

• Lubabalo Mafu,
• Ben Zeelie and
• Paul Watts

Beilstein J. Org. Chem. 2016, 12, 2046–2054, doi:10.3762/bjoc.12.193

• sustainability perspective, but clearly it is necessary to develop protocols that are as environmentally friendly and sustainable as possible. The terpene, citronellal (3,7-dimethyl-6-octenal, 1) is widely used as a feedstock material in the synthesis of fine chemicals such as menthol (2) and para-menthane-3,8

• degradation in performance. However, we are conducting further studies to see how long the reaction could be conducted from a production perspective. Synthesis of propyl, pentyl and hexyl diester derivatives Having successfully synthesised the diacetate 9, other acid anhydrides were evaluated in the process

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• a fixed bed reactor at 110 °C. The authors indicated the perspective of full industrial application for such a system. Phosphonium salts as catalysts for the selective transesterification of carbonates As mentioned above, the transesterification reaction between organic carbonates and alcohols or

From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• ). It turned out that, as is true with many organic chemists I know, I fell in love with the logic of organic chemistry (I cannot understate the influence of Professor Charles Perrin, who taught organic chemistry from a mechanistic perspective with beautiful clarity). I also suspect that the visual

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

• Josef Schachtner,
• Patrick Bayer and
• Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

• set-up of a flow reactor for photochemical reactions at gas/liquid interfaces in any standard student or research laboratory. The requirements, specifications, and pitfalls of the most critical technical components will be discussed from the perspective of a non-expert user (Scheme 2). Solution pump

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Supramolecular chemistry at the interface of biology, materials and medicine

• Eric V. Anslyn and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 1101–1102, doi:10.3762/bjoc.12.105

• their own unique perspective and subarea. There is an enormous amount still to learn about the fundamental nature of noncovalent interactions and particularly how to design and synthesize molecules that complex other molecules or are able to assemble spontaneously into three-dimensional structures. Thus

• it is going in the future. They also offer an intimate portrait of the people behind the work. We know that our authors greatly enjoyed telling their stories and we hope that the readers, particularly students, will find this perspective interesting and perhaps even helpful and inspirational. Eric V

Enantioselective carbenoid insertion into C(sp³)–H bonds

• J. V. Santiago and
• A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

• bonds, the mechanistic aspects recently discovered to the known catalytic systems and the application of these synthetic tools to the organic synthesis of natural products. Review Historic perspective on the carbenoid reaction insertion into X–H bonds One of the former works to address the chemistry of

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• was that I had “discovered” molecular concavity and host–guest chemistry, research that I instantly related to the action of the Cytochrome P-450s and other enzymes. Unfortunately however, there was the small problem of financial support. From John’s perspective I had literally appeared out of the

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• postdoctoral researcher was an important step in my professional life. I ended up working closely with him, which ultimately provided me with immense perspective. I will admit that it took a long and hard climb from New Zealand into the UCLA group; it was all action and every step took me closer to my

• “image training” (thanks to Makoto Fujita for the turn of phrase) as much as to show off the shape and function of molecules. Future perspective There are a few grand challenges inspiring us going forward. Underpinning each of them is a central philosophy: that the chemical nature of all matter motivates

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• predatory lifestyle of these organisms [27][36]. In this review, we will address this unresolved question both from a genomic perspective and on the basis of chemical investigations. Terrestrial myxobacteria and the genus Herpetosiphon will be in the focus of our analysis, whereas Lysobacter spp., which

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• direction, with a good perspective, is being carried out in our laboratory. Experimental Chemicals 2-HP-α-CD, 2-HP-β-CD, 2-HP-γ-CD, DIMEB and TRIMEB CDs were purchased from Sigma-Aldrich (Milan, Italy) and used without further purification. The same commercial source was adopted for D2O and LiClO4 (99.99

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• MHz, 298 K). Cartoon models for the possible intermolecular inclusion mode of Rho-β-CD in solution (3D perspective view on the left and 3D structural model on the right). 1H NMR spectrum of Flu-β-CD with partial assignments (D2O, 500 MHz, 298 K). Cartoon models for the possible intermolecular

• inclusion mode of Flu-β-CD in solution (3D perspective view on the left and 3D structural model on the right). Supporting Information Supporting Information File 140: Experimental section, including IR and NMR spectra of the synthesized compounds. Acknowledgement The support of the Marie Curie Programme

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• position in Bath. This was a great move for me from a personal as well as career perspective, since Bath was a very supportive and friendly department. I was also lucky to be appointed at the same time as Toby Jenkins and Steven Bull who have been very good friends and collaborators over the last 15 years

• vague, this makes them open to different interpretations and as such they are as topical and up-to-date as when they were written. “Study the past, if you would divine the future.” – Confucius (551–479 BC) This quote is close to my heart – you will see from this perspective that many of the advances in

• . I would particularly like to thank The Catalysis and Sensing for our Environment (CASE) network [83] for providing excellent networking opportunities, since many of the results contained in this personal perspective are a direct result of the network.

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• , this perspective carves out the path I took from my early childhood fascinations with science through my independent career at the University of Michigan (maize and blue). The influential research projects and mentors are highlighted, including some fortuitous experimental results that drew me into the

• perspective concludes with some predictions about where molecular gels, as well as my personal and professional life, are headed. Keywords: molecular gel; organic chemistry; organic materials; self-assembly; supramolecular chemistry; Review One of my earliest memories involves pouring water down our