Direct synthesis of 6-sulfonylated phenanthridines via silver-catalyzed radical sulfonylation-cyclization of 2-isocyanobiphenyls

被引：16
|
作者：
Singh, Manjula [1 ]
Yadav, Arvind K. [2 ]
Yadav, Lal Dhar S. [2 ]
Singh, Rana Krishna Pal [1 ]
机构：
[1] Univ Allahabad, Dept Chem, Electrochem Lab, Allahabad 211002, Uttar Pradesh, India
[2] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 33期
关键词：
Cyclization; Isonitriles; Phenanthridines; Radical reaction; Sodium sulfinates; Sulfonylation; C BOND FORMATION; TRANSITION-METAL-FREE; QUINOLINE N-OXIDES; VISIBLE-LIGHT; OXIDATIVE CYCLIZATION; SULFUR-DIOXIDE; ARYL ISONITRILES; 6-PHOSPHORYLATED PHENANTHRIDINES; ISOCYANIDE INSERTION; H FUNCTIONALIZATION;
D O I：
10.1016/j.tetlet.2018.07.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and straightforward synthesis of 6-sulfonylated phenanthridines via silver-catalyzed sequential radical insertion, cyclization and aromatization of 2-isocyanobiphenyls is reported. The protocol does not require a phenanthridine scaffold as a substrate and presents a highly regioselective synthesis of 6-alkyl/arylsulfonyl phenanthridines. The protocol utilizes readily available and easy to handle sodium sulfinates as sulfonating agents and potassium persulfate as an oxidant to afford good to excellent yields of the desired products in a one-pot operation at room temperature. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3198 / 3201
页数：4
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