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Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide

โœ Scribed by Hitoshi Kubota; Kenner C. Rice

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
186 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

We examined the palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide using 2-methoxyphenyl trifluoromethanesulfonate (4) as a model compound. The reaction with two equivalents of Zn(CN) 2 and catalytic Pd(PPh3) 4 in DMF at 120ยฐC for 2 hr affonJed 2-methoxybenzonitrile ($) in 81% yield. The synthesis of 3-cyano-3-desoxynaltrexone (3), which had not previouly been obtained by the reaction with potassium or sodium cyanide as a cyanide source, was achieved by applying this ~ to its ~nding triflate 2. Published by Elsevier Science Ltd.

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ChemInform Abstract: Palladium-Catalyzed Cyanation of Hindered, Electron-Rich Aryl Triflates by Zinc Cyanide.
โœ H. KUBOTA; K. C. RICE ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 29 KB ๐Ÿ‘ 2 views

Palladium-Catalyzed Cyanation of Hindered, Electron-Rich Aryl Triflates by Zinc Cyanide. -The Pd-catalyzed cyanation of 2methoxyphenyl triflate (I) as model for hindered, electron-rich aryl triflates, using zinc cyanide is evaluated. Application of the optimized conditions to the triflate (IV) allo