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 - Schilde, Uwe A1 - Kelling, Alexandra T1 - Dual Role of Acetanilides: Traceless Removal of a Directing Group through Deacetylation/Diazotation and Palladium-Catalyzed C-C-Coupling Reactions JF - The journal of organic chemistry N2 - The acetamide group enables regioselective oxidative ortho-C-H activation reactions, such as Pd-catalyzed acylation. The synthetic utility of these transformations can be significantly enhanced by using the acetamide as a quasi-leaving group in a subsequent conventional Pd-catalyzed coupling or cross-coupling reaction. The concept is illustrated herein for the synthesis of o-alkenyl- and o-arylphenones, which have potential for the synthesis of arylated aromatic heterocycles. Y1 - 2015 U6 - https://doi.org/10.1021/acs.joc.5b00272 SN - 0022-3263 VL - 80 IS - 9 SP - 4223 EP - 4234 PB - American Chemical Society CY - Washington ER - TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli A1 - Berger, René A1 - Petersen, Monib H. T1 - From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction JF - Synthesis N2 - A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization. KW - acetanilides KW - deacetylation KW - diazonium salts KW - palladium KW - Matsuda-Heck reaction Y1 - 2013 U6 - https://doi.org/10.1055/s-0032-1316874 SN - 0039-7881 VL - 45 IS - 9 SP - 1174 EP - 1180 PB - Thieme CY - Stuttgart ER - TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli A1 - Berger, René A1 - Hoelter, Frank T1 - Scope and limitations of the Heck-Matsuda-coupling of phenol diazonium salts and styrenes a protecting-group economic synthesis of phenolic stilbenes JF - Organic & biomolecular chemistry : an international journal of synthetic, physical and biomolecular organic chemistry N2 - 4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4'-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 - 2013 U6 - https://doi.org/10.1039/c3ob40420j SN - 1477-0520 VL - 11 IS - 22 SP - 3674 EP - 3691 PB - Royal Society of Chemistry CY - Cambridge 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 - GEN 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 BT - a protecting-group economic synthesis of phenolic stilbenes N2 - 4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4’-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. T3 - Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe - 242 KW - catalyzed cross metathesis KW - o bond formation KW - arenediazonium salts KW - stereoselective-synthesis KW - arylboronic acids KW - substituted stilbenes KW - aryldiazonium salts KW - palladium catalyst KW - trans-stilbenes KW - boronic acid Y1 - 2013 U6 - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:kobv:517-opus4-95070 SP - 3674 EP - 3691 ER - TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli T1 - Selective arene functionalization through sequential oxidative and non-oxidative Heck reactions JF - Chemical communications N2 - A sequence of acetamide directed oxidative Heck reaction and deacetylation-diazotation-Heck coupling allows the traceless removal of the acetamide group and its dual exploitation as a catalyst directing group and a leaving group. Y1 - 2012 U6 - https://doi.org/10.1039/c2cc30752a SN - 1359-7345 VL - 48 IS - 36 SP - 4350 EP - 4352 PB - Royal Society of Chemistry CY - Cambridge ER -