Silver-Catalyzed Tandem Trifluoromethylation and Cyclization of Aryl Isonitriles with the Langlois Reagent
A mild and efficient procedure for the silver-catalyzed tandem trifluoromethylation and cyclization of aryl isonitriles with the Langlois reagent (sodium triflinate) is developed. A series of trifluoromethylated phenanthridines is prepared in moderate to good yields from a cheap and stable trifluoromethyl source.
Efficient generation of perfluoroalkyl radicals from sodium perfluoroalkanesulfinates and a hypervalent iodine(III) reagent: Mild, metal-free synthesis of perfluoroalkylated organic molecules
This article describes an efficient method for the introduction of perfluoroalkyl groups into N-acrylamides, 2-isocyanides, olefins, and other heterocycles using perfluoroalkyl radicals that were generated from the reaction between sodium perfluoroalkanesulfinates and a hypervalent iodine(iii) reagent. This approach represents a simple, scalable perfluoroalkylation method under mild and metal-free conditions.
Visible-light-induced tandem radical addition-cyclization of 2-aryl phenyl isocyanides catalysed by recyclable covalent organic frameworks
A visible-light-induced tandem radical addition-cyclization sequence via 2-aryl phenyl isocyanides as the starting material and two-dimensional covalent organic frameworks (2D-COFs) as the photocatalyst was developed, delivering multifarious 6-substituted phenanthridines in high yields. Benefitting from the utilization of a heterogeneous photocatalyst, this protocol features easy catalyst separation and excellent recyclability. A negligible loss of the catalytic activity was observed after multiple runs. High practicability of this protocol was further demonstrated by continuous flow experiments.
Synthesis of 6-Trifluoromethylphenanthridines through Radical Trifluoromethylation of Isocyanides with Sodium Triflinate under Visible Light
Trifluoromethylation enabled by photochemistry enriched the toolbox of synthetic chemists, to allow the simple and efficient installation of CF3 groups in organic molecules. Herein, we report a cascade addition/annulation reaction of 2-isocyanobiphenyls towards the synthesis of 6-trifluoromethylphenanthridines. It is proposed that this reaction is triggered by the CF3 radical generated from photoexcited 2,3-butanedione (diacetyl) and sodium triflinate. In contrast to classical aromatic trifluoromethylations, this work does not require any additives and features formation of a C–CF3 bond with concomitant construction of an aromatic scaffold.
Li, Jianbin,Caiuby, Clarice A. D.,Paix?o, Márcio W.,Li, Chao-Jun
supporting information
p. 2498 - 2503
(2018/02/06)
Transition Metal-Free Oxidative Radical Decarboxylation/Cyclization for the Construction of 6-Alkyl/Aryl Phenanthridines
A radical cascade decarboxylation/cyclization of 2-isocyanobiphenyls with aliphatic carboxylic acids as well as aromatic carboxylic acids under the transition metal-free conditions was reported. This process, which included formation of two new C-C bonds and cleavage of C-COOH bonds, afforded a novel and environmentally friendly approach to producing 6-alkyl/aryl phenanthridines with moderate to good yields.
Lu, Shichao,Gong, Yaling,Zhou, Demin
p. 9336 - 9341
(2015/09/28)
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