Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid
Тип публикации: Journal Article
Дата публикации: 2008-08-01
scimago Q3
wos Q3
БС2
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
The mild and efficient deblocking of aryl benzyl ethers with TFA is reported. Cleavage was fastest with ortho-electron-withdrawing groups on the phenolic ring, which we have attributed to a proton chelation effect, furnishing the deprotected phenols in excellent yields. The corresponding para-methoxybenzyl, allyl and iso-propyl ethers were also cleanly removed under these conditions. In addition, the selective aryl benzyl ether debenzylation in the presence of benzyl ester, Cbz carbamate and Boc carbamate functionalities was also observed.
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Fletcher S., Gunning P. T. Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid // Tetrahedron Letters. 2008. Vol. 49. No. 33. pp. 4817-4819.
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Fletcher S., Gunning P. T. Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid // Tetrahedron Letters. 2008. Vol. 49. No. 33. pp. 4817-4819.
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TY - JOUR
DO - 10.1016/j.tetlet.2008.06.022
UR - https://doi.org/10.1016/j.tetlet.2008.06.022
TI - Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid
T2 - Tetrahedron Letters
AU - Fletcher, Steven
AU - Gunning, Patrick T.
PY - 2008
DA - 2008/08/01
PB - Elsevier
SP - 4817-4819
IS - 33
VL - 49
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2008_Fletcher,
author = {Steven Fletcher and Patrick T. Gunning},
title = {Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid},
journal = {Tetrahedron Letters},
year = {2008},
volume = {49},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.tetlet.2008.06.022},
number = {33},
pages = {4817--4819},
doi = {10.1016/j.tetlet.2008.06.022}
}
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MLA
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Fletcher, Steven, and Patrick T. Gunning. “Mild, efficient and rapid O-debenzylation of ortho-substituted phenols with trifluoroacetic acid.” Tetrahedron Letters, vol. 49, no. 33, Aug. 2008, pp. 4817-4819. https://doi.org/10.1016/j.tetlet.2008.06.022.