A Solid‐Phase Assisted Flow Approach to In Situ Wittig‐Type Olefination Coupling. Issue 29 (4th August 2021)

• Record Type: Journal Article
• Authors: Tadros, Joseph; Dankers, Christian; Aldrich‐Wright, Janice R.; Polyzos, Anastasios; Gordon, Christopher P.
• Is Part Of: European journal of organic chemistry. Issue 29(2021)
• Page Start: 4184
• Page End: 4194
• Publication Date: 2021-08-04
• Subjects: Flow synthesis -- Immobilised triphenylphosphine -- Olefination -- Solid-Phase synthesis -- Wittig reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100761
• Languages: English
• ISSNs: 1434-193X

Abstract

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 K2 CO3 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. Abstract : The development and subsequent application of an in situ and solid‐phase triphenylphosphine (PS‐PPh3 ) assisted continuous flow protocol to facilitate the coupling of reciprocal primary and secondary halides with aldehyde and ketone‐based substrates is described.