Design and synthesis of C₃-symmetric molecules bearing propellane moieties via cyclotrimerization and a ring-closing metathesis sequence

• Sambasivarao Kotha,
• Saidulu Todeti and
• Vikas R. Aswar

Beilstein J. Org. Chem. 2018, 14, 2537–2544, doi:10.3762/bjoc.14.230

• Bombay, for recording spectral data. S.K. thanks the Department of Science and Technology for the award of a J. C. Bose fellowship (SR/S2/JCB-33/2010), Praj industries, Pune for Pramod Chaudhari Chair Professorship (Green Chemistry) and CSIR (02(0272)/16/EMR-II). S.T. thanks the IIT Bombay for the award

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• interests include: organic synthesis, green chemistry, development of new synthetic methods for unusual amino acids, peptide modifications, cross-coupling reactions, and metathesis. Currently, he occupies the Pramod Chaudhari Chair Professor in Green Chemistry. Milind P. Meshram was born in Amravati

• organic synthesis and green chemistry. Various catalysts used for metathesis reactions. Various angucyclines. SM coupling and RCM protocol to substituted indene derivative 10. Synthesis of polycycles via SM and RCM approach. SM coupling and RCM protocol to the benz[a]anthracene skeleton 26. Synthesis of

• -II] for the financial support. SK thanks the Department of Science and Technology (DST), New Delhi for the award of a J. C. Bose fellowship (SR/S2/JCB-33/2010), and Praj Industries, Pune for the Pramod Chaudhari Chair Professorship (Green Chemistry).

Semi-synthesis and insecticidal activity of spinetoram J and its D-forosamine replacement analogues

• Kai Zhang,
• Jiarong Li,
• Honglin Liu,
• Haiyou Wang and
• Lamusi A

Beilstein J. Org. Chem. 2018, 14, 2321–2330, doi:10.3762/bjoc.14.207

• awarded the Presidential Green Chemistry Challenge Award in 1999 and 2008 [12]. At present, spinetoram is obtained from spinosyn J and spinosyn L by a chemical modification. However, the fermentation productivity of spinosyn J and spinosyn L is low. So a chemical synthesis of spinetoram would be helpful

Hydroarylations by cobalt-catalyzed C–H activation

• Rajagopal Santhoshkumar and
• Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

• synthesis owing to the necessity of green chemistry for the modern universe [1][2][3]. In this context, catalytic C–H functionalization has been acknowledged as an atom- and step-economical process [4][5][6]. A wide range of transition metal-catalyzed non-directed or directing group assisted C–H activation

Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation

• Mrunesh Koli,
• Sucheta Chatterjee,
• Subrata Chattopadhyay and
• Dibakar Goswami

Beilstein J. Org. Chem. 2018, 14, 2198–2203, doi:10.3762/bjoc.14.193

• [20] etc. are also tedious and not ideal for green chemistry. The use of a second metal with lower reduction potential than the active metals could not reduce the amounts of disposable metallic wastes [21][22]. Since most of the in situ-generated allylmetals are hydrolytically unstable, a large excess

Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

• Ugo Azzena,
• Massimo Carraro,
• Gloria Modugno,
• Luisa Pisano and
• Luigi Urtis

Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

• one-pot reaction conditions. Keywords: green chemistry; green solvents; heterogeneous catalysts; multistep reactions; tetrahydropyranylation; Introduction Due to their general stability to a wide range of reagents and ease of removal, tetrahydropyranyl (THP) ethers are widely employed in multistep

Mild and selective reduction of aldehydes utilising sodium dithionite under flow conditions

• Nicole C. Neyt and
• Darren L. Riley

Beilstein J. Org. Chem. 2018, 14, 1529–1536, doi:10.3762/bjoc.14.129

• Chemical Society (ACS), the Green Chemistry Institute (GCI) and several global pharmaceutical companies as one of the primary areas for research and development for chemical manufacturing [1][2][3][4]. For the past decade flow chemistry and the application of flow devices has been gaining acceptance in

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• isophthalic acids (SIBX) [39] has been reported. Nevertheless, from a green chemistry viewpoint, pentavalent iodine oxidants are not ideal because oxidation reactions require a stoichiometric amount of the oxidant that produces an equimolar amount of organoiodine waste. The catalytic use of pentavalent iodine

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

• : specifically, solid solutions, cocrystals, polymorph transitions, carbon nanotube dissolution and inclusion complex formation. Keywords: DNA; green chemistry; mechanochemistry; nucleoside; nucleotide; Introduction Several definitions of mechanochemistry have been attempted since Ostwald included it as one of

• elements of the subject relevant to the current work including applications in organic synthesis [5][6][7][8], green chemistry [9], API formulation [10] and coordination/materials chemistry [11][12]. Some aspects of the current work have also been reviewed recently [13]. However, the impact of

• arduous ion-exchange and drying processes required to render these materials soluble in organic solvents. Likewise, significant reductions in solvent processing (especially if these are high boiling and often toxic and/or carcinogenic) is an attractive green chemistry target. In this context, Thorwith et

Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence

• Amarendar Reddy Maddirala and
• Peter R. Andreana

Beilstein J. Org. Chem. 2018, 14, 875–883, doi:10.3762/bjoc.14.74

• Amarendar Reddy Maddirala Peter R. Andreana Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, USA 10.3762/bjoc.14.74 Abstract The synthesis of spiro[indoline-3,2'-pyrrole]-2,5'(1'H)-diones and

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

• Jingbo Yu,
• Zikun Hong,
• Xinjie Yang,
• Yu Jiang,
• Zhijiang Jiang and
• Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

• transition-metal-catalyzed reactions [1][2], which has shown itself as a powerful synthetic tool in both academic and industrial practice [3][4][5][6][7]. The transformation has been enrolled as key steps for numerous synthetic routes, including the recent President Green Chemistry Award winner route of

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• concept of green chemistry has been recently defined to guide chemists towards minimizing any harmful outcome of chemical processes in either industry or research. Towards greener reactions, scientists have developed various approaches in order to decrease environmental risks while attaining chemical

• , namely: (polymer) vesicles, micelles, dendrimers and nanogels. The ability and efficiency of catalytic nanoreactors to carry out organic reactions in water, to perform cascade reaction and their ability to be recycled will be discussed. Keywords: catalysis; dendrimers; green chemistry; nanogels

• often related to the use of a green non-harmful solvent [3], water. In principle, green chemistry refers to (1) the employment of raw material (substrates) in an efficient manner, (2) decreasing the resulting waste or undesired byproducts, and (3) using cheap and environment friendly solvents (i.e

Liquid-assisted grinding and ion pairing regulates percentage conversion and diastereoselectivity of the Wittig reaction under mechanochemical conditions

• Kendra Leahy Denlinger,
• Lianna Ortiz-Trankina,
• Preston Carr,
• Kingsley Benson,
• Daniel C. Waddell and
• James Mack

Beilstein J. Org. Chem. 2018, 14, 688–696, doi:10.3762/bjoc.14.57

• the Wittig reaction. Keywords: green chemistry; high-speed ball milling; HSBM; LAG; liquid-assisted grinding; Wittig; Introduction Mechanochemistry is maturing as a discipline and continuing to develop and grow [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Thus it is important to continue

Mannich base-connected syntheses mediated by ortho-quinone methides

• Petra Barta,
• Ferenc Fülöp and
• István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

• reactions is definitely more advantageous. Ionic liquids have also attracted considerable attention due to their „green chemistry” values, including reusability, high thermal stability and non-inflammability. Hajipour et al. reported the one-pot synthesis of 1-amidoalkyl-2-naphthols catalysed by N-(4

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure

• Denisa Vargová,
• Rastislav Baran and
• Radovan Šebesta

Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42

• ][21]. Other green chemistry concepts such as reusable media [22], immobilized catalysts [23], or flow set-ups have also been used with success for the synthesis of GABA derivatives [24]. Pregabalin is currently manufactured using enzymatic kinetic resolution [25], but an organocatalytic procedure

Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

• Ernesto Emmanuel López-López,
• José Alvano Pérez-Bautista,
• Fernando Sartillo-Piscil and
• Bernardo A. Frontana-Uribe

Beilstein J. Org. Chem. 2018, 14, 547–552, doi:10.3762/bjoc.14.41

• reaction conditions. Importantly, they also represent a useful way to fulfilling important aspects of the green chemistry [26][27][28], making the synthetic pathways safer and more economical. Therefore, electrosynthetic reactions can be advantageous not only for solving synthetic problems where a redox

• molecule 5. In this letter we report the electrochemical behavior of thiocarbonates 4 and 6 in aqueous methanol MeOH/H2O (80:20) with 0.5 M AcOH/AcONa buffer as supporting electrolyte, as well as the results of several reductive electrolysis performed under green chemistry conditions. Cyclic thiocarbonate

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp² C–H bond activation in ball mills

• Zi Liu,
• Hui Xu and
• Guan-Wu Wang

Beilstein J. Org. Chem. 2018, 14, 430–435, doi:10.3762/bjoc.14.31

• construction of C–X bonds. With the development of transition-metal-catalyzed cross-coupling reactions, a series of halogenations at the ortho-position of the directing groups have been disclosed [5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Nevertheless, from the viewpoint of green chemistry, the

Progress in copper-catalyzed trifluoromethylation

• Guan-bao Li,
• Chao Zhang,
• Chun Song and
• Yu-dao Ma

Beilstein J. Org. Chem. 2018, 14, 155–181, doi:10.3762/bjoc.14.11

• imidazoheterocycles and meet the guiding principles of green chemistry, this reaction was conducted in a recyclable mixed medium of 1-butyl-3-methylimidazolium tetrafluoroborate ([Bmim]BF4) and water. In the presence of catalytic amounts of cupric acetate and TBHP, various substrates, such as 6-arylimidazo[2,1-b

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

• Neil S. Keddie,
• Pier Alexandre Champagne,
• Justine Desroches,
• Jean-François Paquin and
• David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

• Facility at Swansea University. This work was also supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the FRQNT Centre in Green Chemistry and Catalysis (CGCC), and the Université Laval.

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• Discussion Synthesis of intermediates and dyes On the basis of Green Chemistry concepts [47][48][49] and with the aim of avoiding the disadvantages of Brooker’s method and reducing the adverse effects of the synthesis, we report here a simple, environmentally more benign (in comparison the Brooker’s method

A semisynthesis of 3'-O-ethyl-5,6-dihydrospinosyn J based on the spinosyn A aglycone

• Kai Zhang,
• Shenglan Liu,
• Anjun Liu,
• Hongxin Chai,
• Jiarong Li and
• Lamusi A

Beilstein J. Org. Chem. 2017, 13, 2603–2609, doi:10.3762/bjoc.13.257

• persistence and low mammalian and avian toxicity [12]. Therefore, spinosad was awarded the Presidential Green Chemistry Challenge Award in 1999. However, spinosad was not effective in killing certain key pests of fruit trees and nut trees. To solve this problem, Dow AgroSciences used an "artificial neural

• addition, spinetoram shows excellent selectivity for the target insects, while being less harmful to beneficial predators, mammals and human beings [16]. Therefore, spinetoram was awarded the Presidential Green Chemistry Challenge Award in 2008. At present, spinetoram is obtained from spinosyn J and

Synthesis of naturally-derived macromolecules through simplified electrochemically mediated ATRP

• Paweł Chmielarz,
• Tomasz Pacześniak,
• Katarzyna Rydel-Ciszek,
• Izabela Zaborniak,
• Paulina Biedka and
• Andrzej Sobkowiak

Beilstein J. Org. Chem. 2017, 13, 2466–2472, doi:10.3762/bjoc.13.243

• the development of the “green chemistry” variety of this method. The catalyst complex concentration has been substantially reduced to parts per million (ppm) level in the reaction system, due to the development of the simplified electrochemically mediated ATRP (seATRP) approach [54], which offers

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• : BioMOFs; drugs; green chemistry; mechanochemistry; organic based materials; Introduction Mechanochemistry is a straightforward and clean technique by which the desired products are obtained in high purity and high or quantitative yield. It combines high reaction efficiency with a minimum input of energy

• and solvent. It is an approach to green chemistry, an area devoted to the discovery of environmentally friendly synthetic pathways, eliminating or drastically reducing the amount of solvent necessary to catalytically promote reactions. Mechanochemistry consists of grinding together two or more

Mechanochemistry

• José G. Hernández

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

• Jose G. Hernandez Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany 10.3762/bjoc.13.234 Keywords: green chemistry; mechanochemistry; organic chemistry; solvent-free; The scientific community’s general interest in using mechanical energy to trigger or

• 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

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• : green chemistry; mechanism; mechanochemistry; milling; monitoring; Raman spectroscopy; Introduction Over the past decade, mechanochemical reactions [1][2][3][4], i.e., chemical transformations induced or sustained through the application of mechanical force in the form of grinding, milling and shearing