Fluorinated Vilsmeier Reagent: TFEDMA-mediated Synthesis of Aryl-cyanides and Aryl-amides via the Activation of Oximes†

被引：0
作者：
Yadav, Arvind K. [1 ,2 ]
Reddy Narra, Srikanth [1 ]
Zulfaqar Bacho, Muhamad [1 ]
Sumii, Yuji [3 ]
Shibata, Norio [1 ,3 ]
机构：
[1] Nagoya Inst Technol, Dept Nanopharmaceut Sci, Showa Ku, Nagoya 4668555, Japan
[2] Baba Raghav Das Post Grad Coll, Dept Chem, Deoria 274001, UP, India
[3] Nagoya Inst Technol Gokiso, Dept Life Sci & Appl Chem, Showa Ku, Nagoya 4668555, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 06期
关键词：
Cyanides; Amides; Fluorine; Dehydration; Oximes; C-H CYANATION; INTRAMOLECULAR ARYLCYANATION; CATALYZED CYANATION; CARBOXYLIC-ACIDS; F-SO2+ DONOR; NITRILES; EFFICIENT; ALDOXIMES; CONVERSION; DEHYDRATION;
D O I：
10.1002/ajoc.202300049
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient method for the activation of aryl-oximes is reported using 1,1,2,2-tetrafluoro-N,N-dimethylethylamine (TFEDMA) as a scalable and efficient reagent. Aryl-aldoximes led to aryl-cyanides while aryl-ketoximes provided aryl-amides in moderate to excellent yields. The iminium form of TFEDMA acted as a fluorinated version of the well-known Vilsmeier reagent. Aryl cyanides and aryl amides are valuable synthetic units in natural products and drug candidates. The cyano group is also useful in polymer chemistry for the preparation of photovoltaic cells and LEDs.
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页数：5
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