TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli A1 - Riemer, Nastja A1 - Hölter, Frank T1 - Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionalization JF - European journal of organic chemistry N2 - Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings. KW - Arenes KW - Amides KW - C-C coupling KW - Cross-coupling KW - Palladium Y1 - 2015 U6 - https://doi.org/10.1002/ejoc.201500795 SN - 1434-193X SN - 1099-0690 IS - 26 SP - 5826 EP - 5841 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli A1 - Berger, René A1 - Hölter, Frank T1 - Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes N2 - 4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4ï-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior. Y1 - 2014 UR - http://pubs.rsc.org/en/content/articlepdf/2013/ob/c3ob40420j U6 - https://doi.org/10.1039/C3OB40420J SN - 1477-0520 ER - TY - THES A1 - Hölter, Frank T1 - Synthese phenologischer Diazoniumsalze und ihre Anwendung in Palladium-kristalisierten Kupplungsreaktionen Y1 - 2011 CY - Potsdam ER - TY - JOUR A1 - Schmidt, Bernd A1 - Hölter, Frank A1 - Kelling, Alexandra A1 - Schilde, Uwe T1 - Pd-Catalyzed arylation reactions with phenol diazonium salts application in the synthesis of diarylheptanoids JF - The journal of organic chemistry N2 - The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement. Y1 - 2011 U6 - https://doi.org/10.1021/jo2002787 SN - 0022-3263 SN - 1520-6904 VL - 76 IS - 9 SP - 3357 EP - 3365 PB - American Chemical Society CY - Washington ER - TY - JOUR A1 - Schmidt, Bernd A1 - Hölter, Frank T1 - Suzuki-Miyaura cross coupling reactions with Phenoldiazonium salts JF - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry N2 - The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis. Y1 - 2011 U6 - https://doi.org/10.1039/c1ob05256j SN - 1477-0520 VL - 9 IS - 13 SP - 4914 EP - 4920 PB - Royal Society of Chemistry CY - Cambridge ER -