@article{SchmidtKrehlSoteloMeza2012, author = {Schmidt, Bernd and Krehl, Stefan and Sotelo-Meza, Veronica}, title = {Synthesis of chromanes through RCM-Transfer hydrogenation}, series = {Synthesis}, volume = {44}, journal = {Synthesis}, number = {11}, publisher = {Thieme}, address = {Stuttgart}, issn = {0039-7881}, doi = {10.1055/s-0031-1289758}, pages = {1603 -- 1613}, year = {2012}, abstract = {A sequential ruthenium-catalyzed ring-closing metathesis-transfer hydrogenation sequence has been established as a synthesis of chromanes starting from 2-(allyloxy)styrenes. The sequence requires only one precatalyst, the first-generation Grubbs catalyst, which is converted into a ruthenium hydride species in situ. Propan-2-ol serves as a chemical trigger for the formation of the ruthenium hydride and as hydrogen source.}, language = {en} } @article{SchmidtKrehlKellingetal.2012, author = {Schmidt, Bernd and Krehl, Stefan and Kelling, Alexandra and Schilde, Uwe}, title = {Synthesis of 8-Aryl-Substituted Coumarins based on Ring-Closing Metathesis and Suzuki-Miyaura coupling - synthesis of a Furyl Coumarin natural product from Galipea panamensis}, series = {The journal of organic chemistry}, volume = {77}, journal = {The journal of organic chemistry}, number = {5}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo2026564}, pages = {2360 -- 2367}, year = {2012}, abstract = {The synthesis of 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, a natural product with antileishmanial activity recently isolated from the plant Galipea panamensis, is described. The key step is a Suzuki-Miyaura coupling of a furan-3-boronic acid and an 8-halocoumarin, which is advantageously synthesized using a ring-closing metathesis reaction. Several non-natural analogues are also available along these lines.}, language = {en} } @misc{Krehl2012, author = {Krehl, Stefan}, title = {Entwicklung von Ruthenium-katalysierten Tandem-Reaktionssequenzen}, address = {Potsdam}, pages = {280 S.}, year = {2012}, language = {de} } @article{SchmidtKrehlJablowski2012, author = {Schmidt, Bernd and Krehl, Stefan and Jablowski, Eric}, title = {Assisted tandem catalytic RCM-aromatization in the synthesis of pyrroles and furans}, series = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry}, volume = {10}, journal = {Organic \& biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry}, number = {26}, publisher = {Royal Society of Chemistry}, address = {Cambridge}, issn = {1477-0520}, doi = {10.1039/c2ob25543j}, pages = {5119 -- 5130}, year = {2012}, abstract = {An assisted tandem catalytic transformation of diallyl amines and diallyl ethers into N-aryl pyrroles and furans, respectively, is described. The sequence relies on ring closing metathesis followed by dehydrogenation of the initially formed dihydropyrroles and dihydrofurans. Both steps are Ru-catalyzed, but the sequence requires only one precatalyst, because conversion of the metathesis catalyst into the dehydrogenation catalyst is achieved in situ, triggered by the oxidant tert-butyl hydroperoxide.}, language = {en} } @article{SchmidtKrehlHauke2013, author = {Schmidt, Bernd and Krehl, Stefan and Hauke, Sylvia}, title = {Assisted tandem catalytic cross metathesis-oxidation in one flask from styrenes to 1,2-Diketones and further to quinoxalines}, series = {The journal of organic chemistry}, volume = {78}, journal = {The journal of organic chemistry}, number = {11}, publisher = {American Chemical Society}, address = {Washington}, issn = {0022-3263}, doi = {10.1021/jo4005684}, pages = {5427 -- 5435}, year = {2013}, abstract = {1,2-Diketones were synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by condensation of the oxidation products with ortho-phenylenediamine.}, language = {en} } @article{SchmidtKrehl2011, author = {Schmidt, Bernd and Krehl, Stefan}, title = {A single precatalyst tandem RCM-allylic oxidation sequence}, series = {Chemical communications}, volume = {47}, journal = {Chemical communications}, number = {20}, publisher = {Royal Society of Chemistry}, address = {Cambridge}, issn = {1359-7345}, doi = {10.1039/c1cc11347j}, pages = {5879 -- 5881}, year = {2011}, abstract = {Ring closing metathesis of allyloxy styrenes and a subsequent Ru-catalyzed allylic oxidation can be combined to a tandem sequence that makes coumarins accessible using less active but more conveniently available first generation catalysts.}, language = {en} } @article{GoebelStoltenbergKrehletal.2016, author = {G{\"o}bel, Ronald and Stoltenberg, Marcus and Krehl, Stefan and Biolley, Christine and Rothe, Regina and Schmidt, Bernd and Hesemann, Peter and Taubert, Andreas}, title = {A Modular Approach towards Mesoporous Silica Monoliths with Organically Modified Pore Walls: Nucleophilic Addition, Olefin Metathesis, and Cycloaddition}, series = {European journal of inorganic chemistry : a journal of ChemPubSoc Europe}, volume = {6}, journal = {European journal of inorganic chemistry : a journal of ChemPubSoc Europe}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-1948}, doi = {10.1002/ejic.201500638}, pages = {2088 -- 2099}, year = {2016}, abstract = {We have synthesized mesoporous silica (monoliths) with defined surface chemistry by means of a number of addition reactions: (i) coupling of an isocyanate to a surface-immobilized thiol, (ii) addition of an epoxide to a surface-immobilized thiol, (iii) cross-metathesis between two olefins, and (iv) Huisgen [2+3] cycloaddition of an alkyne-functionalized silica monolith with an azide. Functionalization of the mesopores was observed, but there are significant differences between individual approaches. Isocyanate and epoxide additions lead to high degrees of functionalization, whereas olefin metathesis and [2+3] cycloaddition are less effective. We further show that the efficiency of the modification is about twice as high in mesoporous silica particles than in macroscopic silica monoliths.}, language = {en} }