✦ LIBER ✦
PPh3-Catalyzed Reactions of Alkyl Propiolates with N-Tosylimines: A Facile Synthesis of Alkyl 2-[aryl(tosylimino)methyl]acrylate and an Insight into the Reaction Mechanism
✍ Scribed by Huimin Liu; QiongMei Zhang; Limin Wang; Xiaofeng Tong
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 283 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
A new PPh~3~‐catalyzed synthesis of alkyl 2‐[aryl(tosylimino)methyl]acrylates from propiolate and N‐tosylimine has been developed. Deuterium‐labelling experiments show that the reaction mechanism involves several hydrogen‐transfer processes, which are not the turnover‐limiting step and strongly rely on the nature of the reaction media. The stable phosphonium–enamine zwitterion, which was proven to play an important role in the catalytic cycle, has been isolated and characterised by X‐ray analysis.