title: Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell.
abstract: Electrochemical deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h-1productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: Robert A
authors.initials: RA
authors.lastname: Green
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: Katherine E
authors.initials: KE
authors.lastname: Jolley
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: Azzam A M
authors.initials: AAM
authors.lastname: Al-Hadedi
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: Derek
authors.initials: D
authors.lastname: Pletcher
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: David C
authors.initials: DC
authors.lastname: Harrowven
authors.affiliation: Centro de Investigación Lilly S.A., Avda. de la Industria 30, 28108 Alcobendas-Madrid, Spain.
authors.forename: Oscar
authors.initials: O
authors.lastname: De Frutos
authors.affiliation: Centro de Investigación Lilly S.A., Avda. de la Industria 30, 28108 Alcobendas-Madrid, Spain.
authors.forename: Carlos
authors.initials: C
authors.lastname: Mateos
authors.affiliation: Early Chemical Development, AstraZeneca, Charter Way, Macclesfield, SK10 2NA, U.K.
authors.forename: David J
authors.initials: DJ
authors.lastname: Klauber
authors.affiliation: Centro de Investigación Lilly S.A., Avda. de la Industria 30, 28108 Alcobendas-Madrid, Spain.
authors.forename: Juan A
authors.initials: JA
authors.lastname: Rincón
authors.affiliation: Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
authors.forename: Richard C D
authors.identifier: 0000-0003-0156-7087
authors.initials: RCD
authors.lastname: Brown