Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

• Jiao-Na Han,
• Cong Du,
• Xinju Zhu,
• Zheng-Long Wang,
• Yue Zhu,
• Zhao-Yang Chu,
• Jun-Long Niu and
• Mao-Ping Song

Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

• structural units present in many natural products, functional materials, and pharmaceuticals [1]. Consequently, a variety of strategies have emerged to access them, including Pd-catalyzed and Cu-catalyzed coupling reactions (Buchwald–Harting couplings and Ullmann reactions) [2][3][4]. However, these classic

• –C or C–heteroatom bonds has attracted more attention [8][9][10][11][12][13]. In particular, the formation of C–O bonds is widely used in the syntheses of pharmaceuticals and functional materials [14][15][16][17]. The direct hydroxylation [18][19] and acetoxylation [20][21][22] have been developed

Functionalization of graphene: does the organic chemistry matter?

• Artur Kasprzak,
• Agnieszka Zuchowska and
• Magdalena Poplawska

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

• (RGO) have most commonly been investigated in terms of creating novel functional materials. GO is a product of oxidative exfoliation from bulk graphite [4]. GO’s structure (Figure 1a) comprises a large number of oxygen functionalities, including carboxyl (COOH), hydroxy (OH) and epoxide (see the

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• conditions [6][17][18][19], such as solvent, light and temperature. These characteristics meet currents demands for conveniently controlling the assembly of materials according to their size, shape, and morphology. Chiral functional materials have aroused much attention for their potential applications. Liu

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• inorganic species such as copper oxide [54] or noble metals (Pt [55] and Pd [56]) able to catalyze organic reactions, our nanosponges undoubtedly appear as promising new platforms for the preparation of composite nanocatalysts or functional materials with improved performances. Experimental All the reagents

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

• Anna Czarnecka,
• Emilia Kowalska,
• Agnieszka Bodzioch,
• Joanna Skalik,
• Marek Koprowski,
• Krzysztof Owsianik and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

• Anna Czarnecka Emilia Kowalska Agnieszka Bodzioch Joanna Skalik Marek Koprowski Krzysztof Owsianik Piotr Balczewski Group of Synthesis of Functional Materials, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland, Department of

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

• Erwann Grenet,
• Ashis Das,
• Paola Caramenti and
• Jérôme Waser

Beilstein J. Org. Chem. 2018, 14, 1208–1214, doi:10.3762/bjoc.14.102

• Nitrogen-containing heteroaromatic compounds have valuable properties in medicinal chemistry, pharmacology and functional materials. Among those, pyridinone, sometimes called pyridone, is a key structural motif of well-known active compounds and natural products (Figure 1) [1]. For example, the 2

Two novel blue phosphorescent host materials containing phenothiazine-5,5-dioxide structure derivatives

• Feng-Ming Xie,
• Qingdong Ou,
• Qiang Zhang,
• Jiang-Kun Zhang,
• Guo-Liang Dai,
• Xin Zhao and
• Huai-Xin Wei

Beilstein J. Org. Chem. 2018, 14, 869–874, doi:10.3762/bjoc.14.73

• Feng-Ming Xie Qingdong Ou Qiang Zhang Jiang-Kun Zhang Guo-Liang Dai Xin Zhao Huai-Xin Wei College of Chemistry, Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou, Jiangsu 215009, P.R. China Jiangsu Key Laboratory of Environmental Functional Materials, Suzhou

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

• Zhensheng Zhao and
• Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

• . Experimental evidence suggests that a radical mechanism is involved. Keywords: allene; chlorination; hypervalent iodine; synthetic methods; vinyl chloride; Introduction Organochlorine compounds are vital as polymer precursors [1], as pharmaceuticals [2][3] and agrochemicals [4][5][6] and as functional

• materials [7][8]. And as there is an abundance of chlorine-containing natural products, the synthesis of chlorinated functional groups, such as allyl- and vinyl chlorides, can represent challenging obstacles that practitioners of natural product synthesis must surmount [9][10][11][12]. More commonly, allyl

Synthesis and stability of strongly acidic benzamide derivatives

• Frederik Diness,
• Niels J. Bjerrum and
• Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

• enable their incorporation into functional materials (e.g., polymers), these acids need additional functionality in the form of a reactive group, and the chemistry applied for functionalization must be compatible with their strong acidic nature. Many types of strong organic acids such as triflic acid (7

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

• Huangguan Chen,
• Jianwei Han and
• Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

• photosensitive dyes. Keywords: benzyne; cycloaddition; diaryliodonium salts; N-phenylamine; pyrrole; Introduction Pyrrole is a very useful heterocyclic substrate to produce structural attributes of valuable chemicals, functional materials and pharmaceuticals [1][2][3][4][5]. Recently, arylation of pyrrole

CF₃SO₂X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF₃SO₂Na

• Hélène Guyon,
• Hélène Chachignon and
• Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

• -featuring molecules [5]. Its oxidised congeners CF3S(O) and CF3SO2 are also well-developed as structural units in biologically active compounds, catalysts for synthesis, and functional materials. The chemistry of CF3Se derivatives is less developed but basically shares the same synthetic approaches with

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

• Takeshi Fujita,
• Ryo Kinoshita,
• Tsuyoshi Takanohashi,
• Naoto Suzuki and
• Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

• carbocycles that are promising candidates for pharmaceuticals, agrochemicals, and functional materials. In contrast, the cationic cyclization of 1,1-difluoro-1-alkenes using electrophilic reagents (under acidic conditions) has been quite limited because of their low electron densities caused by fluorine

Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

• Tao Fan,
• Wei-Dong Meng and
• Xingang Zhang

Beilstein J. Org. Chem. 2017, 13, 2610–2616, doi:10.3762/bjoc.13.258

• past decade, investigations mainly focused on direct fluorination or fluoroalkylation of aromatics [1][2][3][4][5]. Fluoroalkylated alkenes are a kind of important fluorinated structural motifs and have wide applications in medicinal chemistry and advanced functional materials [6][7][8][9]. However

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• phospholium salt, and the borane complex showed a high fluorescence emission. Further investigations are underway to develop functional materials including electronic devices and evaluate the physicochemical properties of these compounds by synthetic, theoretical, and spectroscopic studies. Phosphole-based

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• to metabolism and oxidation compared to non-fluorinated compounds. In addition to their stability, perfluorinated compounds exhibit non-tackiness, low friction, and the ability to repel water and oil [24]. Therefore, they are used as functional materials such as fluorocarbon polymer. Fluorine is also

• compounds. By introducing a fluorine atom, phthalocyanines are also expected to become novel functional materials that reflect the specific properties of the fluorine atom. Fluorine-containing phthalocyanines have been found to behave differently from non-fluorine phthalocyanines due to the specific

• , various TFEO-Pcs can be conveniently prepared, setting a path for the development of more functional materials. Synthesis of di- and trinuclear trifluoroethoxy-substituted phthalocyanines and investigation of their aggregation properties Di- or trinuclear phthalocyanines can be highly functionalized

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

• Functional Materials: Synthesis and Characterization with Focus on the Specific Interactions between Solid Surfaces and Biomacromolecules“ (RICALTRO_CTC_2017_RAS_MONDUZZI) and by Fondazione Banco di Sardegna with the projects: RICALTRO_CTC_2017_FBS_MONDUZZI. The “Teach Mob – Teaching Staff Mobility Programme

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• -catalyzed cross-coupling reactions to form C–C bonds are very powerful synthetic tools in modern organic synthesis [7]. With their increasing applications in the synthesis of pharmaceuticals, natural products and functional materials [8][9][10], moving these useful transformations to occurring in aqueous

Synthesis and metal binding properties of N-alkylcarboxyspiropyrans

• Alexis Perry and
• Christina J. Kousseff

Beilstein J. Org. Chem. 2017, 13, 1542–1550, doi:10.3762/bjoc.13.154

• stabilisation and that only beyond a threshold distance does hydrogen bond donation of the carboxylic acid become important. This is a key point in designing functional materials based on N-alkylcarboxyspiropyrans. Conclusion In summary, we have developed a high-yielding, two-step synthesis of N

• spiropyran–merocyanine equilibria. Consequently, the results of this study will impact upon the design and synthesis of dynamic functional materials based on spiropyran–merocyanine units, with particular relevance to cases where such materials are used in the presence of metal cations (e.g., in biological

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• Maryna V. Murlykina Maryna N. Kornet Sergey M. Desenko Svetlana V. Shishkina Oleg V. Shishkin Aleksander A. Brazhko Vladimir I. Musatov Erik V. Van der Eycken Valentin A. Chebanov Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• . Keywords: fullerenes; hexakisadducts; hydrogen bonding; porous materials; structure elucidation; Introduction The utilization of confined nanospace in rigid frameworks [1], which are derived from small molecular precursors under dynamic conditions, has emerged as a novel design paradigm for functional

• materials with the prospect of applications in gas storage [2][3], catalysis [4][5], luminescence [6][7][8][9] and sensing [10][11][12][13] or optoelectronics [14][15][16]. Owing to a modular approach, building blocks and cross-linking interactions can be varied over a wide range resulting in metal-organic

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• Xiao Huang Li Yang Rikard Emanuelsson Jonas Bergquist Maria Stromme Martin Sjodin Adolf Gogoll Department of Chemistry - BMC, Uppsala University, Box 576, 751 23 Uppsala, Sweden Nanotechnology and Functional Materials, Department of Engineering Sciences, Uppsala University, Box 534, 751 21 Uppsala

Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• the last years especially as the parent alcohol of isosorbide. The latter is also a platform chemical with applications in pharmaceuticals, detergents, fuel additives, monomers and building blocks for new polymers and functional materials and new high boiling organic solvents. Conversion of D-sorbitol

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

• Maddali L. N. Rao,
• Jalindar B. Talode and
• Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

• : bromobenzofuran coupling; cross-coupling; palladium; regio-selective; triarylbismuth; Introduction The benzofuran scaffold is present in various biologically active molecules [1][2][3][4][5][6][7][8], natural products [9][10][11][12][13][14][15] and also part of various functional materials [16]. Importantly

Synthesis of 2-substituted tetraphenylenes via transition-metal-catalyzed derivatization of tetraphenylene

• Shulei Pan,
• Hang Jiang,
• Yanghui Zhang,
• Yu Zhang and
• Dushen Chen

Beilstein J. Org. Chem. 2016, 12, 1302–1308, doi:10.3762/bjoc.12.122

• ). Having successfully developed protocols for introducing OAc and X (Cl, Br, I) onto tetraphenylene (1), we next turned to investigate the carbonylation of tetraphenylene (1). The carbonyl group is a common structural element present in both natural products and functional materials and can be transformed

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• versatile receptors for molecular recognition and building blocks for functional materials. Due to the binding of two adjacent CD units, bridged bis-CDs display high binding abilities and molecular selectivities compared to native and monosubstituted CDs. A well-organized pseudo-cavity may be provided by