Safe Palladium-Catalyzed Cross-Couplings with Microwave Heating Using Continuous-Flow Silicon Carbide Reactors
2014 (English)In: Organic Process Research & Development, ISSN 1083-6160, E-ISSN 1520-586X, Vol. 18, no 11, 1413-1418 p.Article in journal (Refereed) Published
Herein we present a 200 mm × 3 mm Øi silicon carbide (SiC) tube reactor for use in a commercially available microwave heated continuous-flow system. The SiC flow reactor enables palladium(0)-catalyzed reactions that, due to precipitation and subsequent hot spot formation, often followed by reactor failure, are unsuitable to conduct in standard microwave-transparent borosilicate glass reactors. We report continuous-flow protocols for the Mizoroki–Heck reaction (10 examples, 81–86% yield) as well as the Suzuki–Miyaura cross-coupling (14 examples, 70–87% yield), showing the utility of the SiC reactor. Furthermore, we performed a scale-out of the NSAID biphenylacetic acid, achieving outputs of 14 mmol/h of the Suzuki–Miyaura reaction, and a 72% overall yield over three steps. The SiC reactor enabled fast and efficient temperature control, high robustness, and easy maintenance.
Place, publisher, year, edition, pages
2014. Vol. 18, no 11, 1413-1418 p.
IdentifiersURN: urn:nbn:se:uu:diva-240554DOI: 10.1021/op5001989ISI: 000345552100020OAI: oai:DiVA.org:uu-240554DiVA: diva2:776702