Electrochemical deprotection of para-methoxybenzyl ethers in a flow electrolysis cell
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 pmethoxybenzaldehyde 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.
2050-2053
Green, Robert A.
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Jolley, Katherine E.
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Hadedi, Azzam A.M.
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Pletcher, Derek
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Harrowven, David C.
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De Frutos, Oscar
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Mateos, Carlos
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Klauber, David J.
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Rincon, Juan A.
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Brown, Richard C.D.
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Green, Robert A.
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Jolley, Katherine E.
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Hadedi, Azzam A.M.
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Pletcher, Derek
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Harrowven, David C.
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De Frutos, Oscar
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Mateos, Carlos
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Klauber, David J.
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Rincon, Juan A.
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Brown, Richard C.D.
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Green, Robert A., Jolley, Katherine E., Hadedi, Azzam A.M., Pletcher, Derek, Harrowven, David C., De Frutos, Oscar, Mateos, Carlos, Klauber, David J., Rincon, Juan A. and Brown, Richard C.D.
(2017)
Electrochemical deprotection of para-methoxybenzyl ethers in a flow electrolysis cell.
Organic Letters, 19 (8), .
(doi:10.1021/acs.orglett.7b00641).
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 pmethoxybenzaldehyde 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.
Text
ol-2017-00641f revised
- Accepted Manuscript
More information
Accepted/In Press date: 30 March 2017
e-pub ahead of print date: 4 April 2017
Organisations:
Chemistry, Organic Chemistry: SCF
Identifiers
Local EPrints ID: 410661
URI: http://eprints.soton.ac.uk/id/eprint/410661
ISSN: 1523-7060
PURE UUID: 4ef92abb-9faa-4022-aaef-c9eb053bc288
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Date deposited: 09 Jun 2017 09:19
Last modified: 16 Mar 2024 05:18
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Contributors
Author:
Robert A. Green
Author:
Katherine E. Jolley
Author:
Azzam A.M. Hadedi
Author:
Oscar De Frutos
Author:
Carlos Mateos
Author:
David J. Klauber
Author:
Juan A. Rincon
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