An environmentally benign and high-rate Appel type reaction. Issue 7 (5th May 2022)

• Record Type: Journal Article
• Authors: Fuenzalida, Nicolas Mattias Del Rio; Alme, Eirin; Lundevall, Frida Johanne; Bjørsvik, Hans-René
• Is Part Of: Reaction chemistry & engineering. Volume 7:Issue 7(2022)
• Page Start: 1650
• Page End: 1659
• Publication Date: 2022-05-05
• Subjects: Reaction mechanisms (Chemistry) -- Periodicals; Chemical engineering -- Periodicals; Chemical engineering; Reaction mechanisms (Chemistry); Periodicals; 547.705
• DOI: 10.1039/d2re00071g
• Languages: English
• ISSNs: 2058-9883

Abstract

Abstract : A green, high rate, high yielding, and selective Appel reaction that make use of 1, 3-dihalo-5, 5-dimethylhydantoins and N -halo-succinimides as halogenation reagents. The new Appel reaction method was developed for batch and continuous flow reactors. Abstract : A high rate, selective, and productive Appel type reaction was developed. The method allows for ipso -substitution of the alcoholic hydroxy group with halogens ∈ [Cl, Br, I]. The method demands mild reaction conditions that include a very short reaction time, <15 min only, versus reaction times of several hours or days using the classical Appel reaction conditions (PPh3 + CCl4 + R–OH). The method was demonstrated to operate with the cheap and easily available 1, 3-dihalo-5, 5-dimethylhydantoins and N -halo succinimides (halo ∈ [Cl, Br, I]) as the reagent that performs the halogenation of PPh3 . The reaction protocol operated with several acceptable solvents rather than DCM that was used in the classical Appel reaction. Furthermore, the batch protocol was also translated and successfully implemented on a flow reactor platform ( t < 5 min, y = 95%).