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ChemInform Abstract: Electrophilic Cyanations. Part 2. Synthesis of Heteroarenecarbonitriles by Electrophilic Cyanation: Reaction of Metalated Heteroarenes with p-Toluenesulfonyl Cyanide.

✍ Scribed by I. NAGASAKI; Y. SUZUKI; K. IWAMOTO; T. HIGASHINO; A. MIYASHITA

Publisher
John Wiley and Sons
Year
2010
Weight
30 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Electrophilic Cyanations. Part 2. Synthesis of Heteroarenecarbonitriles by Electrophilic Cyanation: Reaction of Metalated Heteroarenes with p-Toluenesulfonyl Cyanide.

-Carefull regioselective lithiation of hetarenes or even arenes (I) followed by addition of Tos-CN gives fair yields of (hetero)arenecarbonitriles (III). Silylated hetarenes (IV) undergo a similar reaction in refluxing THF. -(NAGASAKI, I.;

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ChemInform Abstract: Electrophilic Cyana
ChemInform Abstract: Electrophilic Cyanations. Part 1. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p- Toluenesulfonyl Cyanide.
✍ A. MIYASHITA; I. NAGASAKI; A. KAWANO; Y. SUZUKI; K. IWAMOTO; T. HIGASHINO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB

Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide. -A variety of mercapto-substituted heteroarenes (I) (15 examples) undergo electrophilic cyanation with tosyl cyanide (II) in THF to yield the thiocyanato derivatives (III). In DMF th