@phdthesis{Wolf2016, author = {Wolf, Felix}, title = {Neuartige Olefine und Aryldiazoniumtetrafluoroborate f{\"u}r die MATSUDA-HECK-Reaktion}, school = {Universit{\"a}t Potsdam}, pages = {158}, year = {2016}, language = {de} } @article{SchmidtWolfBrunner2016, author = {Schmidt, Bernd and Wolf, Felix and Brunner, Heiko}, title = {Styrylsulfonates and -Sulfonamides through Pd-Catalysed Matsuda-Heck Reactions of Vinylsulfonic Acid Derivatives and Arenediazonium Salts}, series = {European journal of organic chemistry}, journal = {European journal of organic chemistry}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201600469}, pages = {2972 -- 2982}, year = {2016}, abstract = {Arene diazonium salts undergo Matsuda-Heck reactions with vinylsulfonates and -sulfonamides to give styrylsulfonic acid derivatives in high to excellent yields and with high to excellent selectivities. By quantifying the evolution of nitrogen over time in a gas-meter apparatus, the reactivities of ethylvinylsulfonate and the benchmark olefin methyl acrylate were compared for an electron-rich and an -deficient arene diazonium salt. Tertiary sulfonamides react in Matsuda-Heck couplings with high conversions, but require long reaction times, which prevents the determination of kinetic data through the measurement of nitrogen evolution. Secondary sulfonamides were found to be unreactive. From these results, the following order of reactivity could be deduced: H2C=CHCO2Me > H2C=CHSO2OEt > H2C=CHSO2N(Me)Bn >> H2C=CHSO2NHBn. Through the Matsuda-Heck coupling of 5-indolyldiazonium salt and a tertiary vinylsulfonamide, the synthesis of the C-5-substituted indole part of the antimigraine drug naratriptan was accomplished in high yield.}, language = {en} } @article{SchmidtWolf2017, author = {Schmidt, Bernd and Wolf, Felix}, title = {Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts}, series = {The journal of organic chemistry}, volume = {82}, journal = {The journal of organic chemistry}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/acs.joc.7b00447}, pages = {4386 -- 4395}, year = {2017}, abstract = {The Pd-catalyzed Heck-type coupling (Matsuda Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.}, language = {en} } @article{SchmidtWolfEhlert2016, author = {Schmidt, Bernd and Wolf, Felix and Ehlert, Christopher}, title = {Systematic Investigation into the Matsuda-Heck Reaction of alpha-Methylene Lactones: How Conformational Constraints Direct the beta-H-Elimination Step}, series = {The journal of organic chemistry}, volume = {81}, journal = {The journal of organic chemistry}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/acs.joc.6b02207}, pages = {11235 -- 11249}, year = {2016}, abstract = {alpha-Methylene-gamma-butyrolactone and alpha-methylene-gamma-valerolactone undergo Pd-catalyzed Matsuda-Heck couplings with arene diazonium salts to alpha-benzyl butenolides or pentenolides, respectively, or to alpha-benzylidene lactones. The observed regioselectivity is strongly ring size dependent, with six-membered rings giving exclusively alpha-benzyl pentenolides, whereas the five-membered alpha-methylene lactone reacts to mixtures of regioisomers with a high proportion of (E)-alpha-benzylidene-gamma-butyrolactones. DFT calculations suggest that the reasons for these differences are not thermodynamic but kinetic in nature. The relative energies of the conformers of the Pd sigma-complexes resulting from insertion into the Pd-aryl bond were correlated with the dihedral angles between Pd and endo-beta-H. This correlation revealed that in the case of the six-membered lactone an energetically favorable conformer adopts a nearly synperiplanar Pd/endo-beta-H arrangement, whereas for the analogous Pd sigma-complex of the five-membered lactone the smallest Pd/endo-beta-H dihedral angle is observed for a conformer with a comparatively high potential energy. The optimized conditions for Matsuda-Heck arylations of exo-methylene lactones were eventually applied to the synthesis of the natural product anemarcoumarin A.}, language = {en} } @misc{HetenyiMolinariClintonetal.2018, author = {Hetenyi, Gyorgy and Molinari, Irene and Clinton, John and Bokelmann, Gotz and Bondar, Istvan and Crawford, Wayne C. and Dessa, Jean-Xavier and Doubre, Cecile and Friederich, Wolfgang and Fuchs, Florian and Giardini, Domenico and Graczer, Zoltan and Handy, Mark R. and Herak, Marijan and Jia, Yan and Kissling, Edi and Kopp, Heidrun and Korn, Michael and Margheriti, Lucia and Meier, Thomas and Mucciarelli, Marco and Paul, Anne and Pesaresi, Damiano and Piromallo, Claudia and Plenefisch, Thomas and Plomerova, Jaroslava and Ritter, Joachim and Rumpker, Georg and Sipka, Vesna and Spallarossa, Daniele and Thomas, Christine and Tilmann, Frederik and Wassermann, Joachim and Weber, Michael and Weber, Zoltan and Wesztergom, Viktor and Zivcic, Mladen and Abreu, Rafael and Allegretti, Ivo and Apoloner, Maria-Theresia and Aubert, Coralie and Besancon, Simon and de Berc, Maxime Bes and Brunel, Didier and Capello, Marco and Carman, Martina and Cavaliere, Adriano and Cheze, Jerome and Chiarabba, Claudio and Cougoulat, Glenn and Cristiano, Luigia and Czifra, Tibor and Danesi, Stefania and Daniel, Romuald and Dannowski, Anke and Dasovic, Iva and Deschamps, Anne and Egdorf, Sven and Fiket, Tomislav and Fischer, Kasper and Funke, Sigward and Govoni, Aladino and Groschl, Gidera and Heimers, Stefan and Heit, Ben and Herak, Davorka and Huber, Johann and Jaric, Dejan and Jedlicka, Petr and Jund, Helene and Klingen, Stefan and Klotz, Bernhard and Kolinsky, Petr and Kotek, Josef and Kuhne, Lothar and Kuk, Kreso and Lange, Dietrich and Loos, Jurgen and Lovati, Sara and Malengros, Deny and Maron, Christophe and Martin, Xavier and Massa, Marco and Mazzarini, Francesco and Metral, Laurent and Moretti, Milena and Munzarova, Helena and Nardi, Anna and Pahor, Jurij and Pequegnat, Catherine and Petersen, Florian and Piccinini, Davide and Pondrelli, Silvia and Prevolnik, Snjezan and Racine, Roman and Regnier, Marc and Reiss, Miriam and Salimbeni, Simone and Santulin, Marco and Scherer, Werner and Schippkus, Sven and Schulte-Kortnack, Detlef and Solarino, Stefano and Spieker, Kathrin and Stipcevic, Josip and Strollo, Angelo and Sule, Balint and Szanyi, Gyongyver and Szucs, Eszter and Thorwart, Martin and Ueding, Stefan and Vallocchia, Massimiliano and Vecsey, Ludek and Voigt, Rene and Weidle, Christian and Weyland, Gauthier and Wiemer, Stefan and Wolf, Felix and Wolyniec, David and Zieke, Thomas}, title = {The AlpArray seismic network}, series = {Surveys in Geophysics}, volume = {39}, journal = {Surveys in Geophysics}, number = {5}, publisher = {Springer}, address = {Dordrecht}, organization = {ETHZ SED Elect Lab AlpArray Seismic Network Team AlpArray OBS Cruise Crew AlpArray Working Grp}, issn = {0169-3298}, doi = {10.1007/s10712-018-9472-4}, pages = {1009 -- 1033}, year = {2018}, abstract = {The AlpArray programme is a multinational, European consortium to advance our understanding of orogenesis and its relationship to mantle dynamics, plate reorganizations, surface processes and seismic hazard in the Alps-Apennines-Carpathians-Dinarides orogenic system. The AlpArray Seismic Network has been deployed with contributions from 36 institutions from 11 countries to map physical properties of the lithosphere and asthenosphere in 3D and thus to obtain new, high-resolution geophysical images of structures from the surface down to the base of the mantle transition zone. With over 600 broadband stations operated for 2 years, this seismic experiment is one of the largest simultaneously operated seismological networks in the academic domain, employing hexagonal coverage with station spacing at less than 52 km. This dense and regularly spaced experiment is made possible by the coordinated coeval deployment of temporary stations from numerous national pools, including ocean-bottom seismometers, which were funded by different national agencies. They combine with permanent networks, which also required the cooperation of many different operators. Together these stations ultimately fill coverage gaps. Following a short overview of previous large-scale seismological experiments in the Alpine region, we here present the goals, construction, deployment, characteristics and data management of the AlpArray Seismic Network, which will provide data that is expected to be unprecedented in quality to image the complex Alpine mountains at depth.}, language = {en} }