A Continuous‐Flow Process for Palladium‐Catalyzed Olefin Cleavage by using Oxygen within the Explosive Regime. Issue 17 (24th July 2017)

• Record Type: Journal Article
• Authors: Hone, Christopher A.; O'Kearney‐McMullan, Anne; Munday, Rachel; Kappe, C. Oliver
• Is Part Of: ChemCatChem. Volume 9:Issue 17(2017)
• Page Start: 3298
• Page End: 3302
• Publication Date: 2017-07-24
• Subjects: alkenes -- cleavage reactions -- continuous flow -- oxidation -- palladium; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201700671
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A continuous‐flow protocol for Pd‐catalyzed olefin cleavage by using molecular oxygen as the sole oxidant to give carbonyl compounds was explored. The developed flow protocol allowed the use of a low catalyst loading (0.1 mol %), and decomposition of the active catalyst was prevented through stabilization by poly(ethylene glycol)‐400 (PEG‐400), which was present as a cosolvent. Radical scavengers inhibited the reaction, which indicated the involvement of a free‐radical path in the reaction mechanism. The applicability of the continuous‐flow protocol was demonstrated on several olefin substrates. The continuous‐flow process enabled safe and scalable olefin cleavage. Abstract : On break : The development of a continuous‐flow protocol for Pd‐catalyzed olefin cleavage by using molecular oxygen as the sole oxidant to give carbonyl compounds is described. The applicability of the continuous‐flow protocol is demonstrated on several olefin substrates. The continuous‐flow process enables safe and scalable olefin cleavage by using pure O2 . MFC= mass‐flow controller, PTSA= p ‐toluenesulfonic acid, PEG400 =poly(ethylene glycol) 400, 1 bar=0.1 MPa.