POLITAG-M-F as Heterogeneous Organocatalyst for the Waste-Minimized Synthesis of β-Azido Carbonyl Compounds in Batch and under Flow Conditions.

Autor: Valentini F; Laboratory of Green S.O.C.-Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy, greensoc.chm.unipg.it., Brufani G; Laboratory of Green S.O.C.-Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy, greensoc.chm.unipg.it., Rossini G; Laboratory of Green S.O.C.-Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy, greensoc.chm.unipg.it., Campana F; Laboratory of Green S.O.C.-Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy, greensoc.chm.unipg.it.; Consorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali (INSTM), 50121 Firenze, Italy., Lanari D; Dipartimento di Scienze Farmaceutiche, Università degli Studi di Perugia, Via del Liceo 1, 06123 Perugia, Italy., Vaccaro L; Laboratory of Green S.O.C.-Dipartimento di Chimica, Biologia e Biotecnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy, greensoc.chm.unipg.it.
Jazyk: angličtina
Zdroj: ACS sustainable chemistry & engineering [ACS Sustain Chem Eng] 2023 Feb 08; Vol. 11 (7), pp. 3074-3084. Date of Electronic Publication: 2023 Feb 08 (Print Publication: 2023).
DOI: 10.1021/acssuschemeng.2c07213
Abstrakt: We herein report a waste minimization protocol for the β-azidation of α,β-unsaturated carbonyl compounds using TMSN 3 . The selection of the appropriate catalyst ( POLITAG-M-F ), in combination with the reaction medium, resulted in enhanced catalytic efficiency and a low environmental footprint. The thermal and mechanical stability of the polymeric support allowed us to recover the POLITAG-M-F catalyst for up to 10 consecutive runs. The CH 3 CN:H 2 O azeotrope has a 2-fold positive effect on the process, increasing the efficiency of the protocol and minimizing waste generation. Indeed, the azeotropic mixture, used as a reaction medium and for the workup procedure, was recovered by distillation, leading to an easy and environmentally friendly procedure for product isolation in high yield and with a low E-factor. A comprehensive evaluation of the environmental profile was performed by the calculation of different green metrics (AE, RME, MRP, 1/SF) and a comparison with other literature available protocols. A flow protocol was defined to scale-up the process, and up to 65 mmol of substrates were efficiently converted with a productivity of 0.3 mmol/min.
Competing Interests: The authors declare no competing financial interest.
(© 2023 The Authors. Published by American Chemical Society.)
Databáze: MEDLINE
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