Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

• Ramona Riclea,
• Julia Gleitzmann,
• Hilke Bruns,
• Corina Junker,
• Barbara Schulz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2012, 8, 941–950, doi:10.3762/bjoc.8.106

• volatiles released by Ruegeria pomeroyi The volatiles emitted by agar plate cultures of Ruegeria pomeroyi DSS-3 grown on ½ YTSS medium were collected on charcoal by using a closed-loop stripping apparatus (CLSA) [24]. After a collection time of about one day the adsorbed compounds were eluted with

• 17 (1.0 equiv) in ethyl acetate (0.15 M) Pd on charcoal (10% Pd, 0.1 equiv) was added. The mixture was stirred in a hydrogen atmosphere (45 bar) for 1 h at 25 °C. The catalyst was removed by filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column

Chemistry of polyhalogenated nitrobutadienes, 10: Synthesis of highly functionalized heterocycles with a rigid 6-amino-3-azabicyclo[3.1.0]hexane moiety

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Armin de Meijere and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2012, 8, 621–628, doi:10.3762/bjoc.8.69

• application of the usual reductive conditions (i.e., hydrogen under atmospheric pressure, palladium on charcoal suspended in, e.g., ethanol) to the protected amine 12 led to a multiple reaction involving the deprotection, a bisdechlorination and final hydrolysis of an intermediate imine. The resulting ketone

Volatile organic compounds produced by the phytopathogenic bacterium Xanthomonas campestris pv. vesicatoria 85-10

• Teresa Weise,
• Marco Kai,
• Anja Gummesson,
• Armin Troeger,
• Stephan von Reuß,
• Silvia Piepenborn,
• Francine Kosterka,
• Martin Sklorz,
• Ralf Zimmermann,
• Wittko Francke and
• Birgit Piechulla

Beilstein J. Org. Chem. 2012, 8, 579–596, doi:10.3762/bjoc.8.65

• inlet and an outlet). During growth, the bacterial culture was stirred with a magnetic stir bar at 600 rpm and incubated at 30 °C. A diaphragm pump (Denver Gardner, Puchheim, Germany) pulled charcoal-purified, sterile air at a flow of 3 L/min through the system. Volatiles released during a 30 hours

• compartment (Petri dish, 145 x 30 mm) with an in- and outlet. Charcoal-purified air was passed over the culture and entered the PTR instrument through the inlet. All analyses of bacterial metabolites were carried out in triplicate. Blank samples of NB and NBG were analyzed twice to identify compounds directly

The volatiles of pathogenic and nonpathogenic mycobacteria and related bacteria

• Thorben Nawrath,
• Georgies F. Mgode,
• Bart Weetjens,
• Stefan H. E. Kaufmann and
• Stefan Schulz

Beilstein J. Org. Chem. 2012, 8, 290–299, doi:10.3762/bjoc.8.31

• membrane filter (Millipore Corp., USA). Cultures were incubated at 37 °C aerobically. Sampling of volatiles Volatile organic compounds emitted by cell cultures of the different mycobacteria were collected by using the CLSA technique [14][15]. The volatiles were adsorbed on charcoal (Chromtech; Precision

• Charcoal Filter, 5 mg) for 24 h, and then eluted with 30 µL of CH2Cl2. The obtained extracts were immediately analyzed by GC–MS, and stored at –30 °C. GC–EIMS analysis GC–EIMS analyses of the samples were carried out on a HP-6890 GC system connected to a HP-5973 mass-selective detector fitted with a BPX5

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• overnight. After cooling, the mixture was filtered, washed with boiling water and dried in vacuo to afford the crude product. The crude product was dissolved in minimal hot chloroform, dried (MgSO4), stirred with decolourising charcoal for 30 min and then filtered through a silica plug (eluting with

• tetrahydrofuran) and the solvent removed under reduced pressure to leave the crude product. The crude product was dissolved in chloroform, stirred with decolourising charcoal for 30 min and then filtered through a silica plug (eluting with chloroform). The solvents were removed under reduced pressure to afford 5

Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

• Lukas Kupracz,
• Jan Hartwig,
• Jens Wegner,
• Sascha Ceylan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1441–1448, doi:10.3762/bjoc.7.168

• ] or copper-on-charcoal (Cu/C) [30], can serve as a catalytic source that promotes the CuAAC. Bogdan et al. combined this observation with flow technology by using a custom-made heated copper flow reactor [31]. We successfully implemented the CuAAC by inductively heating copper wire inside a flow

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• indole synthesis to yield tetrahydro-4-oxocarbazole 140. Various methods have been described to dehydrogenate this intermediate including the use of bromine, sulfur, LiCl/CuCl, lead dioxide, chloranil or palladium on charcoal. However, the need to use these reagents in equal stoichiometry or even excess

C–C (alkynylation) vs C–O (ether) bond formation under Pd/C–Cu catalysis: synthesis and pharmacological evaluation of 4-alkynylthieno[2,3-d]pyrimidines

• Dhilli Rao Gorja,
• K. Shiva Kumar,
• K. Mukkanti and
• Manojit Pal

Beilstein J. Org. Chem. 2011, 7, 338–345, doi:10.3762/bjoc.7.44

• on the surface of the charcoal. Once generated, the organo-Pd(II) species E then facilitates the stepwise formation of C–C bond via (i) trans organometallation with copper acetylide generated in situ from CuI and the terminal alkyne followed by (ii) reductive elimination of Pd(0) to afford 4

Tribenzotriquinacenes bearing three peripheral or bridgehead urea groups stretched into the 3-D space

• Jörg Tellenbröker and
• Dietmar Kuck

Beilstein J. Org. Chem. 2011, 7, 329–337, doi:10.3762/bjoc.7.43

• ) chloride and charcoal in refluxing methanol (Scheme 1) [23], and afforded a mixture of the triamino-TBTQs 10 and 11 in good yield (81%). However, catalytic hydrogenolysis of compounds 8 and 9 at ambient temperature under medium pressure [20][24][25] proved to be even more efficient and gave the TBTQ

• -tetramethyl-4b,8b,12b,12d-tetrahydrodibenzo[2,3:4,5]pentaleno[1,6-ab]indene (11). Procedure A. A suspension containing the mixture of isomeric trinitrotribenzotriquinacenes 8 and 9 described above (230 mg, 488 mmol), charcoal (32 mg) and iron(III) chloride hexahydrate (10 mg) in methanol (10 mL) was heated to

• reduction of the mixture, yielding the TBTQ triamines 10 and 11. Reagents, conditions and yields: (i) NaNO3, TFA, 25 °C, 48 h, quantitative. (ii) N2H4 · H2O (96%), FeCl3 · 6 H2O, charcoal, 80 °C, 24 h, 81%. Alternatively: (ii) H2, Pd/C, EtOH, 5 bar, 20 °C, 24 h, 91%; yields after chromatography 20% (10) and

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

• Axel G. Griesbeck,
• Marco Franke,
• Jörg Neudörfl and
• Hidehiro Kotaka

Beilstein J. Org. Chem. 2011, 7, 127–134, doi:10.3762/bjoc.7.18

• , isoxazole-carbonyl photocycloaddition products constitute another class of photochromic T-type systems (Scheme 7) [18]. Hydrogenation of 9a by palladium/charcoal did not lead to the expected aminoketone 10, but to the enamino ketone 11 and benzyl alcohol, indicating decomposition of 9a back to the starting

A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH

• Thisbe K. Lindhorst,
• Kathrin Bruegge,
• Andreas Fuchs and
• Oliver Sperling

Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90

• methanol (10 mL) and Pd on charcoal (10%, 10 mg) added. Hydrogenation with vigorous stirring for 3 h led to the title amine, which was obtained after filtration through celite, evaporation and reversed-phase chromatography on silica gel (H2O:MeOH = 1:1) as a colourless lyophilisate (86 mg, 0.16 mmol, 92

Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• using NaOMe followed by hydrogenation to generate 1–8 in good yields. Deprotection was also successful when the hydrogenation was performed first, but in some cases migration of acetate to the aminoethyl linker was observed. However, this can be avoided by using palladium hydroxide on charcoal as the

Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

• Tilman Lechel,
• Irene Brüdgam and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 42, doi:10.3762/bjoc.6.42

• catalytic amounts of palladium on charcoal. Methyl ethers such as 1b or 1d were cleaved by Lewis-acids. The (2-trimethylsilyl)ethyl-protected pyridine 1c was easily deprotected to diol 2c by a Brønsted acid such as TFA. In most cases, the corresponding pyridindiols 2a–d were obtained in good yields (63

• route to isoquinoline derivatives. Experimental Deprotection of 3-alkoxypyridin-4-ols 1, typical procedures Cleavage of the benzyloxy group by hydrogenolysis A mixture of 1a (970 mg, 3.43 mmol) and palladium (365 mg, 10% on charcoal, 0.34 mmol) in methanol (6 mL) was stirred for one day under an

Efficient and improved synthesis of Telmisartan

• A. Sanjeev Kumar,
• Samir Ghosh and
• G. N. Mehta

Beilstein J. Org. Chem. 2010, 6, No. 25, doi:10.3762/bjoc.6.25

• the mixture refluxed for 16 h and then concentrated. The residue was diluted with methanol (40 mL) and transferred to a stainless steel autoclave. Palladium on charcoal (10%, 1.0 g) was added and the reaction mixture stirred under H2 pressure (7 bar) for 24 h at 60 °C. After cooling to room

Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

• Heloise Brice,
• Jonathan Clayden and
• Stuart D. Hamilton

Beilstein J. Org. Chem. 2010, 6, No. 22, doi:10.3762/bjoc.6.22

• with EtOAc (15 mL). 10% Palladium on charcoal (0.053 g, 0.05 mmol) was added and the suspension immediately placed under a hydrogen atmosphere. The suspension was warmed to 45 °C for 18 h, filtered through Celite and evaporated under reduced pressure. The residue was purified by flash chromatography

• with EtOAc (2 × 30 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in propan-2-ol (7 mL), 10% palladium on charcoal (0.053 g, 0.05 mmol) was added and the suspension was immediately placed under a hydrogen atmosphere. The suspension was warmed to 50 °C for 24 h

Pd/C- Mediated synthesis of indoles in water

• Mohosin Layek,
• Udaya Lakshmi,
• Dipak Kalita,
• Deepak K. Barange,
• Aminul Islam,
• K. Mukkanti and
• Manojit Pal

Beilstein J. Org. Chem. 2009, 5, No. 46, doi:10.3762/bjoc.5.46

• -mediated coupling reaction. Keywords: C–C bond; charcoal; copper; indoles; palladium; Introduction 2-Substituted indoles (A, Figure 1) display a wide range of pharmacological activities and therefore have been explored as a number of potential therapeutic agents [1] e.g. inhibitors of proteases involved

Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions

• Klaas Mennecke and
• Andreas Kirschning

Beilstein J. Org. Chem. 2009, 5, No. 21, doi:10.3762/bjoc.5.21

• materials have clear advantages over Pd(0) on charcoal because the latter cannot be further optimized with respect to the mode of application [31][32][33]. In the present study, our highly optimized composite material was chosen (5.3% DVB crosslinker and a 1:1 mixture of VBC/styrene) doped with

Diastereoselective synthesis of some novel benzopyranopyridine derivatives

• Pradeep K. Mohakhud,
• Sujeet M. R. Kumar,
• Vasanth M. R. Kumar,
• Ravi M. R. Kumar,
• Moses D. R. Babu,
• Vyas D. R. K and
• Om D. R. Reddy

Beilstein J. Org. Chem. 2006, 2, No. 25, doi:10.1186/1860-5397-2-25

• benzopyranopyridine derivative 5a using 10% palladium on charcoal in a methanol-HCl mixture (Scheme 2). Initial hydrogenation experiments provided N-benzyl saturated pyridine derivative 8 and N-unsubstituted unsaturated product 6. After extended reaction time, debenzylated saturated product 7 was formed with the cis