A solid-phase assisted flow approach to in situ Wittig-type olefination coupling

Joseph Tadros, Christian Dankers, Janice R. Aldrich-Wright, Anastasios Polyzos, Christopher P. Gordon

Research output: Contribution to journalArticlepeer-review

Abstract

Described herein is the development of a continuous flow, solid-phase triphenylphosphine (PS-PPh3) assisted protocol to facilitate the in situ coupling of reciprocal pairs of halogen and carbonyl functionalised molecular pairs by a Wittig olefination within 15 mins. The protocol entails injecting a single solution (1 : 1 CHCl3 : EtOH) containing the halogenated and carbonyl-based substrates into a continuously flowing stream of CHCl3 : EtOH (1 : 1), passed through a fixed bed of K2CO3 and PS-PPh3. With advancement to the previous PS-PPh3 coupling procedures, the method employs a traditional polystyrene-based immobilisation matrix, the substrate scope of the protocol extended to substituted ketones, secondary alkyl chlorides, and an unprotected maleimide scaffold.
Original languageEnglish
Pages (from-to)4184-4194
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2021
Issue number29
DOIs
Publication statusPublished - 2021

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