TY - JOUR A1 - Sand, Patrick A1 - Schmidt, Bernd T1 - Ruthenium-catalyzed sulfoalkenylation of acetanilides and dual-use of the catalyst directing group JF - European journal of organic chemistry N2 - 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. KW - Arenes KW - C-H activation KW - Heterocycles KW - Ruthenium KW - Sulfonamides Y1 - 2021 U6 - https://doi.org/10.1002/ejoc.202101216 SN - 1434-193X SN - 1099-0690 VL - 2021 IS - 40 SP - 5497 EP - 5506 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Sand, Patrick A1 - Schmidt, Bernd T1 - Orthogonal arylation of a diene-sulfonamide using cationic transition metal catalysts JF - European journal of organic chemistry N2 - 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. KW - arenes KW - C-H activation KW - palladium KW - ruthenium KW - sulfonamides Y1 - 2022 U6 - https://doi.org/10.1002/ejoc.202201336 SN - 1434-193X SN - 1099-0690 VL - 2022 IS - 47 PB - Wiley-VCH CY - Weinheim ER -