@article{SandSchmidt2021, author = {Sand, Patrick and Schmidt, Bernd}, title = {Ruthenium-catalyzed sulfoalkenylation of acetanilides and dual-use of the catalyst directing group}, series = {European journal of organic chemistry}, volume = {2021}, journal = {European journal of organic chemistry}, number = {40}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.202101216}, pages = {5497 -- 5506}, year = {2021}, abstract = {In contrast to vinylsulfonates and vinylsulfones, vinylsulfonamides are unreactive in Pd-catalyzed oxidative Heck-coupling reactions with acetanilides. This limitation has been resolved by using a C-H-activation protocol based on Ru-Cu-Ag-catalysis. Overall, the Ru-Cu-Ag-catalyzed conditions turned out to be more reliable and showed better reproducibility than the Pd-catalyzed C-H-activation. The coupling products thus obtained are functionalized styrenyl sulfones and -sulfonamides which can be used as starting materials for the synthesis of sulfonyl pyrroles and sulfonyl pyrrolo[2,3-c]quinolines.}, language = {en} } @article{SandSchmidt2022, author = {Sand, Patrick and Schmidt, Bernd}, title = {Orthogonal arylation of a diene-sulfonamide using cationic transition metal catalysts}, series = {European journal of organic chemistry}, volume = {2022}, journal = {European journal of organic chemistry}, number = {47}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.202201336}, pages = {8}, year = {2022}, abstract = {The regioselectivity of two mechanistically distinct alkenylation reactions catalyzed by in situ-formed cationic transition metal complexes was studied using N-allyl-N-phenylethenesulfonamide as a model compound. Orthogonal selectivity was observed for the Ru-catalyzed C-H-activating alkenylation with acetanilides, which occurs preferentially at the electron deficient double bond, and for a Pd-catalyzed Heck-type coupling with arene diazonium salts, which occurs preferentially at the more electron rich double bond of the N-allyl substituent.}, language = {en} }