Tetrahedron Letters, volume 35, issue 7, pages 1095-1098
Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic
Publication type: Journal Article
Publication date: 1994-02-01
Journal:
Tetrahedron Letters
Quartile SCImago
Q3
Quartile WOS
Q3
SJR: 0.323
CiteScore: 3.5
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Pentafluorobenzoic acid reacts with YbCp 2 (dme) to yield, after hydrolysis, 2,3,4,5-tetrafluorobenzoic acid. Conversion is near quantitative with activated magnesium as a coreductant and there is evidence for catalytic turnover in ytterbium on addition of a cyclopentadiene source. Reduction of 2,6-F 2 C 6 H 3 CO 2 H to o -FC 6 H 4 CO 2 H and of o -FC 6 H 4 CO 2 H to PhCO 2 H has also been achieved. 2,3,4,5-Tetrafluorobenzoic acid has been obtained in near quantitative yield from reaction of C 6 F 5 CO 2 H with YbCp 2 (dme) and activated magnesium followed by hydrolysis, and there is catalytic turnover in ytterbium on addition of a cyclopentadiene source.
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Deacon G. B., Batten S. H., Sun J. Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic // Tetrahedron Letters. 1994. Vol. 35. No. 7. pp. 1095-1098.
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Deacon G. B., Batten S. H., Sun J. Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic // Tetrahedron Letters. 1994. Vol. 35. No. 7. pp. 1095-1098.
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TY - JOUR
DO - 10.1016/S0040-4039(00)79974-6
UR - https://doi.org/10.1016/S0040-4039(00)79974-6
TI - Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic
T2 - Tetrahedron Letters
AU - Deacon, Glen B.
AU - Batten, Stuart H.
AU - Sun, Jun
PY - 1994
DA - 1994/02/01
PB - Elsevier
SP - 1095-1098
IS - 7
VL - 35
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex
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@article{1994_Deacon,
author = {Glen B. Deacon and Stuart H. Batten and Jun Sun},
title = {Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic},
journal = {Tetrahedron Letters},
year = {1994},
volume = {35},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/S0040-4039(00)79974-6},
number = {7},
pages = {1095--1098},
doi = {10.1016/S0040-4039(00)79974-6}
}
Cite this
MLA
Copy
Deacon, Glen B., et al. “Regiospecific replacement of fluorine by hydrogen in an aromatic ring induced by a rare earth organometallic.” Tetrahedron Letters, vol. 35, no. 7, Feb. 1994, pp. 1095-1098. https://doi.org/10.1016/S0040-4039(00)79974-6.