Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• ; Introduction Nowadays great attention is paid to the use of renewable resources for obtaining fine chemicals and fuels (see numerous reviews [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]). The biorefinery of renewable lignin-carbohydrate materials affords various low-molecular weight organic

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

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

• gaseous and liquid components. The high energy efficiency, low hazard potential, and precise control of reaction parameters have also prompted several adoptions of microflow techniques in technical manufactures of fine chemicals, polymers [26], and pharmaceutical intermediates [27][28][29][30]. The vast

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

• Qiao-Wen Jin,
• Zhuo Chai,
• You-Ming Huang,
• Gang Zou and
• Gang Zhao

Beilstein J. Org. Chem. 2016, 12, 725–731, doi:10.3762/bjoc.12.72

• Qiao-Wen Jin Zhuo Chai You-Ming Huang Gang Zou Gang Zhao Laboratory of Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People’s Republic of China Key Laboratory of Synthetic Chemistry of Natural Substances

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

• Hans Sterckx,
• Johan De Houwer,
• Carl Mensch,
• Wouter Herrebout,
• Kourosch Abbaspour Tehrani and
• Bert U. W. Maes

Beilstein J. Org. Chem. 2016, 12, 144–153, doi:10.3762/bjoc.12.16

• preparation of more complex molecules, typical for fine chemicals, the use of aerobic oxidations is more the exception than the norm [9]. This is partly due to the limited synthetic scope and selectivity of the available oxidation methods. Further research into selective and mild aerobic oxidations is

Comparison of the catalytic activity for the Suzuki–Miyaura reaction of (η⁵-Cp)Pd(IPr)Cl with (η³-cinnamyl)Pd(IPr)(Cl) and (η³-1-t-Bu-indenyl)Pd(IPr)(Cl)

• Patrick R. Melvin,
• Nilay Hazari,
• Hannah M. C. Lant,
• Ian L. Peczak and
• Hemali P. Shah

Beilstein J. Org. Chem. 2015, 11, 2476–2486, doi:10.3762/bjoc.11.269

• , and toluene were dried by passage through a column of activated alumina followed by storage under dinitrogen. All commercial chemicals were used as received; exceptions where noted. MeOH (J. T. Baker) and iPrOH (Macron Fine Chemicals) were not dried but were degassed by sparging with dinitrogen for

N-Heterocyclic carbenes

• Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 2474–2475, doi:10.3762/bjoc.11.268

• stabilizing effects due to their steric and electronic tunable properties) might be unnecessary. The use of these ligands now extends to numerous fields spanning from fine chemicals to polymer synthesis. The area of main group chemistry has also benefited from these ligands as stabilizing entities. Since the

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• Xiang Sun Guoqiao Lai Zhifang Li Yuwen Ma Xiao Yuan Yongjia Shen Chengyun Wang Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China Key Laboratory of Organosilicon Chemistry and Material

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

• Meriem K. Abderrezak,
• Kristýna Šichová,
• Nancy Dominguez-Boblett,
• Antoine Dupé,
• Zahia Kabouche,
• Christian Bruneau and
• Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

• straightforward way for the synthesis of difunctional compounds suitable for polymer syntheses [12][13], fine chemicals [14][15][16][17], or as key synthetic tool in multistep syntheses of complex molecules [18][19][20][21]. Cross metathesis with functional olefins is of great interest as it offers the

Engineering Pichia pastoris for improved NADH regeneration: A novel chassis strain for whole-cell catalysis

• Martina Geier,
• Christoph Brandner,
• Gernot A. Strohmeier,
• Mélanie Hall,
• Franz S. Hartner and
• Anton Glieder

Beilstein J. Org. Chem. 2015, 11, 1741–1748, doi:10.3762/bjoc.11.190

• utilization pathway; whole-cell biotransformation; Introduction Bioreductions represent a sustainable strategy to obtain enantiopure molecules which serve as chiral building blocks for fine chemicals and drugs [1][2]. Such reactions are catalyzed by oxidoreductases, which mainly depend on nicotinamide

DBU-promoted carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone

• Wen-Zhen Zhang,
• Si Liu and
• Xiao-Bing Lu

Beilstein J. Org. Chem. 2015, 11, 906–912, doi:10.3762/bjoc.11.102

• Wen-Zhen Zhang Si Liu Xiao-Bing Lu State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, P. R. China 10.3762/bjoc.11.102 Abstract The carboxylative cyclization of o-hydroxy- and o-acetamidoacetophenone with carbon dioxide promoted by the organic base 1,8

• suitable bases to promote the carboxylation of α-C–H bonds in aromatic ketones with carbon dioxide [17][18][19][20]. In extension of our continuous efforts in developing catalytic transformations of carbon dioxide into value-added fine chemicals [20][22][23], we report herein the DBU-promoted carboxylative

Highly selective generation of vanillin by anodic degradation of lignin: a combined approach of electrochemistry and product isolation by adsorption

• Dominik Schmitt,
• Carolin Regenbrecht,
• Marius Hartmer,
• Florian Stecker and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 473–480, doi:10.3762/bjoc.11.53

• be an alternative for petroleum-based production of fuels as well as fine chemicals [5][6][7]. Since the middle of the last century, the large amount of aromatic structural features making up the polymer led to much effort concerning efficient degradation methods into high value fine chemicals like

Visible light photoredox-catalyzed deoxygenation of alcohols

• Daniel Rackl,
• Viktor Kais,
• Peter Kreitmeier and
• Oliver Reiser

Beilstein J. Org. Chem. 2014, 10, 2157–2165, doi:10.3762/bjoc.10.223

• supply of hydrocarbons from fossil resources calls for the usage of renewable resources for the synthesis of fine chemicals in the future [1]. This strategy suffers from the relative high degree of functionalization of feedstock materials, which is often not desired in fine chemicals and further leads to

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

• Affording valued biaryls and heterobiaryls, namely ubiquitous chemical moieties in pharmaceuticals, natural products, photoactive species and many other functional molecules, the Suzuki–Miyaura cross-coupling reaction is widely employed by the fine chemicals and pharmaceutical industries [1]. The reaction

• . 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

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis

• Verena Weidmann,
• Mathias Schaffrath,
• Holger Zorn,
• Julia Rehbein and
• Wolfgang Maison

Beilstein J. Org. Chem. 2013, 9, 2233–2241, doi:10.3762/bjoc.9.262

• addition, metal-free and biocatalytic methods have been reported [5]. Several of these biocatalytic protocols have been applied to the synthesis of fine chemicals [20][21][22], drugs [23], and food ingredients [24][25][26]. A particularly interesting biocatalytic system for allylic oxidation is the edible

Synthesis of axially chiral gold complexes and their applications in asymmetric catalyses

• Yin-wei Sun,
• Qin Xu and
• Min Shi

Beilstein J. Org. Chem. 2013, 9, 2224–2232, doi:10.3762/bjoc.9.261

• Yin-wei Sun Qin Xu Min Shi Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, and 130 MeiLong Road, Shanghai 200237, People’s Republic of China, State Key Laboratory of Organometallic

Non-cross-linked polystyrene-supported 2-imidazolidinone chiral auxiliary: synthesis and application in asymmetric alkylation reactions

• Quynh Pham Bao Nguyen and
• Taek Hyeon Kim

Beilstein J. Org. Chem. 2013, 9, 2113–2119, doi:10.3762/bjoc.9.248

• Quynh Pham Bao Nguyen Taek Hyeon Kim School of Applied Chemistry and Center for Functional Nano Fine Chemicals, Chonnam National University, Gwangju 500-757, Republic of Korea 10.3762/bjoc.9.248 Abstract Asymmetric alkylation reactions using non-cross-linked polystyrene (NCPS)-supported 2

Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives

• Yin-wei Sun,
• Qin Xu and
• Min Shi

Beilstein J. Org. Chem. 2013, 9, 1969–1976, doi:10.3762/bjoc.9.233

• Yin-wei Sun Qin Xu Min Shi Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 MeiLong Road, Shanghai 200237, People’s Republic of China, State Key Laboratory of Organometallic

AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds

• Qiuping Ding,
• Dan Wang,
• Puying Luo,
• Meiling Liu,
• Shouzhi Pu and
• Liyun Zhou

Beilstein J. Org. Chem. 2013, 9, 1949–1956, doi:10.3762/bjoc.9.231

• single operation, play an important role in atom-economical organic chemistry. A cascade reaction is the most efficient way for targeting fine chemicals, agrochemicals, pharmaceutical drugs, drug intermediates and ingredients by a one-pot reaction in environmentally and economically friendly synthetic

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

• Lin Yan,
• Zhiqiang Han,
• Bo Zhu,
• Caiyun Yang,
• Choon-Hong Tan and
• Zhiyong Jiang

Beilstein J. Org. Chem. 2013, 9, 1853–1857, doi:10.3762/bjoc.9.216

• properties, compared with their parent compounds [1]. Due to the rareness of organofluorine compounds in nature, synthetic fluorinated compounds have been widely applied in numerous areas, including materials, agrochemicals, pharmaceuticals and fine chemicals [2][3][4]. In this context, the stereoselective

The application of a monolithic triphenylphosphine reagent for conducting Ramirez gem-dibromoolefination reactions in flow

• Kimberley A. Roper,
• Malcolm B. Berry and
• Steven V. Ley

Beilstein J. Org. Chem. 2013, 9, 1781–1790, doi:10.3762/bjoc.9.207

• using monolithic supports over traditional beads in flow chemistry protocols can greatly facilitate the synthesis of fine chemicals using these enabling technologies [36]. We have recently reported on the development of a monolithic triphenylphosphine reagent and its application to the Staudinger aza

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

• years in this field and are herein discussed, describing intriguing free-radical routes for the generation of N-oxyl active species under mild conditions. The fields of application range from large-scale production, such as the selective oxidation of alkyl aromatics, to the synthesis of fine chemicals

Iron-containing mesoporous aluminosilicate catalyzed direct alkenylation of phenols: Facile synthesis of 1,1-diarylalkenes

• Satyajit Haldar and
• Subratanath Koner

Beilstein J. Org. Chem. 2013, 9, 49–55, doi:10.3762/bjoc.9.6

• considerable attention by synthetic organic chemists for a long time. The resulting 1,1-disubstituted alkene derivatives (Figure 1) are widely used as key starting materials in the synthesis of fine chemicals [1][2][3][4][5][6][7], polymers [8][9][10][11][12][13][14], and pharmaceuticals [15][16][17

Arylglycine-derivative synthesis via oxidative sp³ C–H functionalization of α-amino esters

• Zhanwei Xu,
• Xiaoqiang Yu,
• Xiujuan Feng and
• Ming Bao

Beilstein J. Org. Chem. 2012, 8, 1564–1568, doi:10.3762/bjoc.8.178

• Zhanwei Xu Xiaoqiang Yu Xiujuan Feng Ming Bao State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, China 10.3762/bjoc.8.178 Abstract An efficient method for the synthesis of arylglycine derivatives is described. The oxidative coupling reactions of naphthols and

Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels–Alder reactions

• Stefan Bräse,
• Nicole Volz,
• Franziska Gläser and
• Martin Nieger

Beilstein J. Org. Chem. 2012, 8, 1385–1392, doi:10.3762/bjoc.8.160

• fine chemicals, were either transition-metal complexes or enzymes. In the past few years, however, organocatalysis has emerged as an alternative approach for the catalytic production of enantiomerically pure organic compounds [15][16]. These organocatalysts have several important advantages. They are