1978-39-8Relevant articles and documents
Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis
Nicewicz, David A.,Pistritto, Vincent A.,Schutzbach-Horton, Megan E.
supporting information, p. 17187 - 17194 (2020/11/02)
Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.
Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia
Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei
supporting information, p. 5934 - 5937 (2015/12/11)
A general and practical catalytic system for aryl amination of aryl chlorides with aqueous or gaseous ammonia has been developed, with CuI as the catalyst and bisaryl oxalic diamides as the ligands. The reaction proceeds at 105-120°C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.
Synthesis of the marine sponge derived β2-adrenoceptor agonist S1319
Fairhurst, Robin A.,Janus, Diana,Lawrence, Annabel
, p. 4697 - 4700 (2007/10/03)
(Chemical Equation Presented) The marine sponge derived β2-adrenoceptor agonist S1319 has been synthesized following a six-step linear sequence. Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole interm