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A Continuous‐Flow Process for Palladium‐Catalyzed Olefin Cleavage by using Oxygen within the Explosive Regime
Author(s) -
Hone Christopher A.,
O'KearneyMcMullan Anne,
Munday Rachel,
Kappe C. Oliver
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700671
Subject(s) - olefin fiber , catalysis , chemistry , ethylene glycol , cleavage (geology) , oxygen , continuous flow , flow chemistry , palladium , explosive material , photochemistry , combinatorial chemistry , organic chemistry , materials science , fracture (geology) , composite material , physics , mechanics
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.