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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 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.
1523-7060
2050-2053
Green, Robert A.
da1a32a9-4643-49fb-842c-8fb733ce553c
Jolley, Katherine E.
c2bbafc9-c814-4183-b56f-6235474ae1d9
Hadedi, Azzam A.M.
84c4d61e-3c6f-43e4-a43c-534f54a716eb
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.
da1a32a9-4643-49fb-842c-8fb733ce553c
Jolley, Katherine E.
c2bbafc9-c814-4183-b56f-6235474ae1d9
Hadedi, Azzam A.M.
84c4d61e-3c6f-43e4-a43c-534f54a716eb
Pletcher, Derek
f22ebe69-b859-4a89-80b0-9e190e6f8f30
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
De Frutos, Oscar
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Mateos, Carlos
92ec7161-7e84-4eee-82c7-9d14ea77d39f
Klauber, David J.
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Rincon, Juan A.
9d8afc61-aba6-433c-ac77-235e28f10028
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), 2050-2053. (doi:10.1021/acs.orglett.7b00641).

Record type: Article

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.

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ol-2017-00641f revised - Accepted Manuscript
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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
ORCID for Katherine E. Jolley: ORCID iD orcid.org/0000-0001-6223-9808
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 09 Jun 2017 09:19
Last modified: 18 Feb 2021 16:47

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Contributors

Author: Robert A. Green
Author: Katherine E. Jolley ORCID iD
Author: Azzam A.M. Hadedi
Author: Derek Pletcher
Author: Oscar De Frutos
Author: Carlos Mateos
Author: David J. Klauber
Author: Juan A. Rincon

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