Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

• David W. Manley and
• John C. Walton

Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173

• constituents of pharmaceuticals and dyestuffs, are non-trivial and involve multiple steps. Consequently, the one-pot SCPC oxidation of phenanthrene (1) to benzocoumarin (2), with a dispersion of TiO2 in aqueous, oxygenated CH3CN [29], is very appealing from a green chemistry point of view (Scheme 1). First

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

• -up with a productivity of 70 g fanetizole (87) in 7 h. In 2013 the Jamison group reported the flow synthesis of the important H1-antagonist diphenhydramine·HCl (92) showcasing the potential of modern flow chemistry to adhere to green chemistry principles (minimal use of organic solvents, atom economy

Electrosynthesis and electrochemistry

• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 949–950, doi:10.3762/bjoc.11.105

• current unsteady supply does not match the demand. Thus, the use of abundant electric power in electrosynthetic processes seems to be rational because high valorisation can be expected. Therefore, electrosynthesis fulfils all requirements for “green chemistry” [4]. When changing feed stocks and natural

Matsuda–Heck reaction with arenediazonium tosylates in water

• Ksenia V. Kutonova,
• Marina E. Trusova,
• Andrey V. Stankevich,
• Pavel S. Postnikov and
• Victor D. Filimonov

Beilstein J. Org. Chem. 2015, 11, 358–362, doi:10.3762/bjoc.11.41

• from commercially available anilines than from haloarenes or triflates. Typically, alcohols, THF or DMF are used as solvents for Matsuda–Heck reactions. One of the most rapidly developing trends in organic synthesis is the carrying out of reactions in water following a «Green chemistry» approach [4

A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

• Yong Miao,
• Florence Djedaïni-Pilard and
• Véronique Bonnet

Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278

• with a promising yield. Keywords: fatty ester; green chemistry; lipase; mono-substituted amphiphilic cyclodextrins; peptide Coupling; solvent-free medium; transesterification; Introduction Cyclodextrins (CDs) are sustainable compounds which are particularly interesting in the frame of pharmaceutical

Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

• Jonathan Potier,
• Stéphane Menuel,
• David Mathiron,
• Véronique Bonnet,
• Frédéric Hapiot and
• Eric Monflier

Beilstein J. Org. Chem. 2014, 10, 2642–2648, doi:10.3762/bjoc.10.276

• ; phosphane; polymer; Introduction Although aqueous organometallic catalysis has been developed long before P. T. Anastas and J. C. Warner set out the foundations of Green Chemistry [1], the very essence of this concept relies on several of the twelve fundamental principles. As such, the use of effective

Synthesis of 2-trifluoromethylpyrazolo[5,1-a]isoquinolines via silver triflate-catalyzed or electrophile-mediated one-pot tandem reaction

• Xiaoli Zhou,
• Meiling Liu,
• Puying Luo,
• Yingjun Lai,
• Tangtao Yang and
• Qiuping Ding

Beilstein J. Org. Chem. 2014, 10, 2286–2292, doi:10.3762/bjoc.10.238

• Xiaoli Zhou Meiling Liu Puying Luo Yingjun Lai Tangtao Yang Qiuping Ding Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi's Key Laboratory of green chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. China Department of Obstetrics and

Supercritical carbon dioxide: a solvent like no other

• Jocelyn Peach and
• Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

• Jocelyn Peach Julian Eastoe School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, U.K. 10.3762/bjoc.10.196 Abstract Supercritical carbon dioxide (scCO2) could be one aspect of a significant and necessary movement towards green chemistry, being a potential replacement for

• on the philosophy of green chemistry, a concept encouraging the design of chemically efficient products and processes that reduce or eliminate the use or generation of hazardous substances [1]. This can, in theory, be achieved through the application of a set of ‘principles’, including reduced use

Clean and fast cross-coupling of aryl halides in one-pot

• Valerica Pandarus,
• Geneviève Gingras,
• François Béland,
• Rosaria Ciriminna and
• Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

• . As the fine chemicals and pharmaceutical industries are eventually adopting green chemistry synthetic methodologies [13], this method provides both industries with a clean route to valued compounds that are widely used in many industrial sectors. Chemical structure of SiliaCat DPP-Pd. Heterogeneously

Substrate dependent reaction channels of the Wolff–Kishner reduction reaction: A theoretical study

• Shinichi Yamabe,
• Guixiang Zeng,
• Wei Guan and
• Shigeyoshi Sakaki

Beilstein J. Org. Chem. 2014, 10, 259–270, doi:10.3762/bjoc.10.21

• (C=O → C=C, alkene) conversion reaction, the Knoevenagel condensation [12] was utilized. While the condensation is traditionally base-catalyzed, it was found to proceed readily in water even without any catalyst [13][14]. Not only can this synthesis be considered as clean (green chemistry), but also

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

• Samir Kundu,
• Babli Roy and
• Basudeb Basu

Beilstein J. Org. Chem. 2014, 10, 26–33, doi:10.3762/bjoc.10.5

• attractive features in terms of the concepts of Green chemistry. Previously, we have developed silica-promoted facile and highly selective methods for N and S-alkylations/acylation from amines or thiols, respectively [37][38]. An equimolar mixture of a benzenethiol and allyl bromide on treatment with silica

Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

• Pier Alexandre Champagne,
• Alexandre Saint-Martin,
• Mélina Drouin and
• Jean-François Paquin

Beilstein J. Org. Chem. 2013, 9, 2451–2456, doi:10.3762/bjoc.9.283

• Engineering Research Council of Canada, the Canada Foundation for Innovation, the FRQNT Centre in Green Chemistry and Catalysis (CGCC), the FQRNT Network for Research on Protein Function, Structure, and Engineering (PROTEO) and the Université Laval.

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• starting materials, and the excellent yields of products. Keywords: green chemistry; pyrrole-fused isocoumarin; reusable solid support; silica sulfuric acid; solvent-free condition; Introduction Isocoumarins are an important class of naturally occurring lactones [1][2][3], which has attracted the

• the synthesis of pyrrole-fused isocoumarins with the help of green methodology, so far. Therefore, the development of an environmentally friendly and safer reaction methodology following the green chemistry principles is essential for the synthesis of pyrrole-fused isocoumarins. The employment of a

• temperature was lower and the yields of the products were higher, the yields were still only moderate. This encouraged us to execute the optimization study in presence of a solid acid catalyst under solvent-free conditions. This is one important facet of green chemistry: the eradication of solvents in

Synthesis of enantiomerically pure N-(2,3-dihydroxypropyl)arylamides via oxidative esterification

• Akula Raghunadh,
• Satish S More,
• T. Krishna Chaitanya,
• Yadla Sateesh Kumar,
• Suresh Babu Meruva,
• L. Vaikunta Rao and
• U. K. Syam Kumar

Beilstein J. Org. Chem. 2013, 9, 2129–2136, doi:10.3762/bjoc.9.250

• opening of chiral epoxide with an aryl or heteroaryl aldehyde by oxidative esterification. This method may prove significant from the perspective of green chemistry. The application of this methodology for the synthesis of several bicyclic frameworks and natural products is under progress, and will be

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• reaction; cellulose nanocrystallites (CNCs) films; gold catalysis; water or without solvent; Introduction Organic synthesis is usually performed in organic solvents; however, from a green chemistry perspective, evaporation and discharge of organic solvents not only generates chemical waste but also causes

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• detrimental for the selectivity of the process and they would not meet the standards of “green chemistry”. An alternative catalytic route is based on the use of N-hydroxy imides (NHIs), and in particular N-hydroxyphthalimide (NHPI), which have found ample application as ideal catalysts for the aerobic

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

• Murugan Sathishkumar,
• Sangaraiah Nagarajan,
• Poovan Shanmugavelan,
• Murugan Dinesh and
• Alagusundaram Ponnuswamy

Beilstein J. Org. Chem. 2013, 9, 689–697, doi:10.3762/bjoc.9.78

• halides [16][17] or carboxylic esters [18]. These protocols are generally solution phase methods using organic solvents and acid scavengers. In the present scenario, such protocols may not be recommended by the principles of green chemistry. Consequently, the search for simple and efficient

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes

• Lennart Möhlmann,
• Stefan Ludwig and
• Siegfried Blechert

Beilstein J. Org. Chem. 2013, 9, 602–607, doi:10.3762/bjoc.9.65

• -free oxidation; N-heterocyclic carbene; organocatalysis; Introduction The development of efficient and selective aerobic oxidation methods for organic substrates is of increasing interest and an attractive goal in green chemistry [1][2][3]. In a recent communication we reported on selective oxidation

• ) for example can nowadays be gained directly from the conversion of biomass and thereby became an attractive synthesis unit in modern "green" chemistry [32]. Hence, further cheap and environmentally friendly selective transformations are of great interest. However, only a few methods have been

Easy and direct conversion of tosylates and mesylates into nitroalkanes

• Alessandro Palmieri,
• Serena Gabrielli and
• Roberto Ballini

Beilstein J. Org. Chem. 2013, 9, 533–536, doi:10.3762/bjoc.9.58

• Alessandro Palmieri Serena Gabrielli Roberto Ballini “Green Chemistry Group”, School of Science and Technology, Chemistry Division, University of Camerino, Via S. Agostino 1, 62032 Camerino (MC), Italy 10.3762/bjoc.9.58 Abstract Tosylates and mesylates were directly converted into the

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

• Paweł Borowiecki,
• Małgorzata Milner-Krawczyk and
• Jan Plenkiewicz

Beilstein J. Org. Chem. 2013, 9, 516–525, doi:10.3762/bjoc.9.56

• , solvent for the ions, and medium. Most of the described optically active ILs are prepared from easily accessible natural chiral substrates [40]. The use of ILs in so-called “green chemistry”, as for example solvents in inorganic or organic syntheses or as a replacement for many hazardous and volatile

Mechanochemistry assisted asymmetric organocatalysis: A sustainable approach

• Pankaj Chauhan and
• Swapandeep Singh Chimni

Beilstein J. Org. Chem. 2012, 8, 2132–2141, doi:10.3762/bjoc.8.240

• : ball-milling; enantioselective synthesis; mechanochemistry; organocatalysis; solvent-free; Introduction Green chemistry involves innovation in chemical research and engineering that encourages the design of processes to minimize the use and production of hazardous materials and also reduce the use of

• . Organocatalyts also provide an insight into biological catalytic processes, as a number of these catalysts work by the phenomenon of enzyme mimicry. These advantages of chiral organocatalysts also meet many of the requirements of green chemistry [27]. Recently developed, organocatalytic asymmetric

Imidazolinium and amidinium salts as Lewis acid organocatalysts

• Oksana Sereda,
• Nicole Clemens,
• Tatjana Heckel and
• René Wilhelm

Beilstein J. Org. Chem. 2012, 8, 1798–1803, doi:10.3762/bjoc.8.205

• electrochemical processes [1]. Several of these solvents can contribute to the research field of “green chemistry” [2]. The most common used ionic liquids are based on imidazolium cations. Next to their application in catalytic reactions [3][4][5][6], they are also capable of catalyzing reactions themselves

Organocatalytic C–H activation reactions

• Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

• being one of the “key green chemistry research areas” [4][5][6]. This review describes the current “state of the art” in organocatalyzed C–H activation reactions and highlights recent advances in sp2 and sp3 C–H bond functionalization. For simplicity, iodide or hypervalent iodine-mediated metal-free C–H

Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone

• Jin-Sheng Yu,
• Feng Zhou,
• Yun-Lin Liu and
• Jian Zhou

Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157

• Jin-Sheng Yu Feng Zhou Yun-Lin Liu Jian Zhou Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. China 10.3762/bjoc.8.157 Abstract We reported the first example of organocatalytic

Catalyst-free and solvent-free Michael addition of 1,3-dicarbonyl compounds to nitroalkenes by a grinding method

• Zong-Bo Xie,
• Na Wang,
• Ming-Yu Wu,
• Ting He,
• Zhang-Gao Le and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2012, 8, 534–538, doi:10.3762/bjoc.8.61

• Zong-Bo Xie Na Wang Ming-Yu Wu Ting He Zhang-Gao Le Xiao-Qi Yu Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China, 610064; Fax: (+86) 28-85415886; Tel: (+86) 28-85415886 School of Chemistry Biology and Material Science

• in order to meet the requirement of green chemistry. Namely, the reaction mixture was filtered through a sand core funnel containing a thin layer of silica gel and the pure product was obtained. More than half of the products could be rapidly purified in this way with similar or higher yields and