Synthesis, volume 2004, issue 10, pages 1609-1618
The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates
Publication type: Journal Article
Publication date: 2004-06-23
Catalysis
Organic Chemistry
Abstract
2,4-Difluorophenol, 2,5-difluorophenol, 2,3-difluorophenol, 3,5-difluorophenol, 3,4-difluorophenol, 2,4,5-trifluorophenol and 2,3,4-trifluorophenol were converted into all 18 possible di- or trifluorinated hydroxybenzoic acids, all of them new compds. The phenolic hydrogen atom was replaced by a methoxymethyl or, less frequently, by a triisopropylsilyl group, which exerted an ortho activating or ortho shielding effect, resp. Sites flanked by two electroneg. substituents (fluorine, alkoxy) were deprotonated with particular ease. They had to be silenced by the reversible attachment of a metalation-blocking trimethylsilyl group or of a metalation-deflecting chlorine atom if the metal was to be introduced elsewhere. In all cases but one, the stage was thus set for an intramol. competition between metalation at an oxygen-adjacent or a fluorine-adjacent site. It proved indeed possible to secure the desired regioflexibility in either way by relying on an appropriate substrate-reagent matching. This demonstrates once more the potential of the organometallic approach to diversity-oriented synthesis. [on SciFinder (R)]
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Schlosser M., Marzi E., Górecka J. The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates // Synthesis. 2004. Vol. 2004. No. 10. pp. 1609-1618.
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Schlosser M., Marzi E., Górecka J. The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates // Synthesis. 2004. Vol. 2004. No. 10. pp. 1609-1618.
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TY - JOUR
DO - 10.1055/s-2004-829110
UR - https://doi.org/10.1055/s-2004-829110
TI - The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates
T2 - Synthesis
AU - Schlosser, Manfred
AU - Marzi, Elena
AU - Górecka, Joanna
PY - 2004
DA - 2004/06/23 00:00:00
PB - Thieme
SP - 1609-1618
IS - 10
VL - 2004
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2004_Schlosser,
author = {Manfred Schlosser and Elena Marzi and Joanna Górecka},
title = {The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates},
journal = {Synthesis},
year = {2004},
volume = {2004},
publisher = {Thieme},
month = {jun},
url = {https://doi.org/10.1055/s-2004-829110},
number = {10},
pages = {1609--1618},
doi = {10.1055/s-2004-829110}
}
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Schlosser, Manfred, et al. “The Regioexhaustive Functionalization of Difluorophenols and Trifluorophenols Through Organometallic Intermediates.” Synthesis, vol. 2004, no. 10, Jun. 2004, pp. 1609-1618. https://doi.org/10.1055/s-2004-829110.