Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell

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 a...

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Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (8), p.2050-2053
Main Authors: Green, Robert A, Jolley, Katherine E, Al-Hadedi, Azzam A. M, Pletcher, Derek, Harrowven, David C, De Frutos, Oscar, Mateos, Carlos, Klauber, David J, Rincón, Juan A, Brown, Richard C. D
Format: Article
Language:English
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Summary: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–1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00641