caa a22 4500 44587855X CHVBK 20180317145535.0 cr unu---uuuuu 170323e20110801xx s 000 0 eng 10.1007/s11030-010-9300-3 doi (NATIONALLICENCE)springer-10.1007/s11030-010-9300-3 Stepwise aromatic nucleophilic substitution in continuous flow. Synthesis of an unsymmetrically substituted 3,5-diamino-benzonitrile library [Elektronische Daten] [László Lengyel, Viktor Gyóllai, Tamás Nagy, György Dormán, Péter Terleczky, Viktor Háda, Katalin Nógrádi, Ferenc Sebők, László Ürge, Ferenc Darvas] Aromatic or heteroaromatic ring precursors with 2-3 identical functionalities are often used in sequential derivatization depending on the reactivity difference or the selective execution of the reaction such as nucleophilic aromatic substitution. Continuous flow chemistry offers an enhanced parameter space (pressure and temperature) with rapid parameter optimization that ensures selectivity in many cases. We developed a flow chemistry procedure to carry out a stepwise aromatic nucleophilic substitution of difluoro-benzenes having an activating group in meta position to the fluorines. The mono-aminated products were obtained in high yield and selectivity in an extremely short reaction time, while applying higher temperature, longer reaction zone (or time), and employing higher excess of another amine reactant, the subsequent introduction of the second amino group was also successfully achieved leading to an unsymmetrically substituted 3,5-diamino-benzonitrile library. Springer Science+Business Media B.V., 2010 Continuous flow chemistry nationallicence Nucleophilic substitution nationallicence Enhanced parameter space nationallicence Fluorine-amine exchange nationallicence Lengyel László ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Gyóllai Viktor ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Nagy Tamás ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Dormán György ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Terleczky Péter Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut Háda Viktor Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut Nógrádi Katalin Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut Sebők Ferenc Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut Ürge László ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Darvas Ferenc ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut Molecular Diversity Springer Netherlands 15/3(2011-08-01), 631-638 1381-1991 15:3<631 2011 15 11030 https://doi.org/10.1007/s11030-010-9300-3 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11030-010-9300-3 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lengyel László ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 700 1- Gyóllai Viktor ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 700 1- Nagy Tamás ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 700 1- Dormán György ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 700 1- Terleczky Péter Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut NATIONALLICENCE 700 1- Háda Viktor Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut NATIONALLICENCE 700 1- Nógrádi Katalin Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut NATIONALLICENCE 700 1- Sebők Ferenc Gedeon Richter plc., Gyömrői út 19-21, 1103, Budapest, Hungary aut NATIONALLICENCE 700 1- Ürge László ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 700 1- Darvas Ferenc ThalesNano Inc., Záhony u. 7, 1031, Budapest, Hungary aut NATIONALLICENCE 773 0- Molecular Diversity Springer Netherlands 15/3(2011-08-01), 631-638 1381-1991 15:3<631 2011 15 11030 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer