Journal of the American Chemical Society, volume 141, issue 5, pages 2143-2151
Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials
Silaeva Kseniia P
1, 2
,
Milenin Sergey A
3
,
Novikov Roman G.
4, 5
,
Solyev Pavel N.
4
,
Tkachev Yaroslav V.
4
,
Korlyukov Alexander
1, 6
,
Muzafarov Aziz M.
1, 3
Publication type: Journal Article
Publication date: 2019-01-08
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Synthesis of organosilicon products with a "polar" functional group within organic substituents is one of the most fundamentally and practically important challenges in today's chemistry of silicones. In our study, we suggest a solution to this problem, viz., a high-efficiency preparative method based on aerobic Co-/ N-hydroxysuccinimide (NHSI) catalyzed oxidation of p-tolylsiloxanes to p-carboxyphenylsiloxanes. This approach is based on "green", commercially available, simple, and inexpensive reagents and employs mild reaction conditions: Co(OAc)2/NHSI catalytic system, O2 as the oxidant, process temperature from 40 to 60 °C, atmospheric pressure. This reaction is general and allows for synthesizing both mono- and di-, tri-, and poly( p-carboxyphenyl)siloxanes with p-carboxyphenyl groups at 1,1-, 1,3-, 1,5-, and 1,1,1-positions. All the products were obtained and isolated in gram amounts (up to 5 g) and in high yields (80-96%) and characterized by NMR, ESI-HRMS, GPC, IR, and X-ray data: p-carboxyphenylsiloxanes in crystalline state form HOF-like structures. Furthermore, it was shown that the suggested method is applicable for the oxidation of organic alkylarene derivatives (Ar-CH3, Ar-CH2-R) to the corresponding acids and ketones (Ar-C(O)OH and Ar-C(O)-R), as well as hydride silanes ([Si]-H) to silanols ([Si]-OH). The possibility of synthesizing monomeric (methyl) and polymeric (siloxane-containing PET analogue, Sila-PET) esters based on 1,3-bis( p-carboxyphenyl)disiloxane was studied. These processes occur with retention of the organosiloxane frame and allow to obtain the corresponding products in 90 and 99% yields.
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Goncharova I. K. et al. Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials // Journal of the American Chemical Society. 2019. Vol. 141. No. 5. pp. 2143-2151.
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Goncharova I. K., Silaeva K. P., Arzumanyan A. V., Anisimov A. A., Milenin S. A., Novikov R. G., Solyev P. N., Tkachev Y. V., Volodin A. D., Korlyukov A., Muzafarov A. M. Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials // Journal of the American Chemical Society. 2019. Vol. 141. No. 5. pp. 2143-2151.
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TY - JOUR
DO - 10.1021/jacs.8b12600
UR - https://doi.org/10.1021%2Fjacs.8b12600
TI - Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials
T2 - Journal of the American Chemical Society
AU - Silaeva, Kseniia P
AU - Arzumanyan, Ashot V
AU - Novikov, Roman G.
AU - Solyev, Pavel N.
AU - Muzafarov, Aziz M.
AU - Goncharova, Irina K
AU - Anisimov, Anton A.
AU - Milenin, Sergey A
AU - Tkachev, Yaroslav V.
AU - Volodin, Alexander D
AU - Korlyukov, Alexander
PY - 2019
DA - 2019/01/08 00:00:00
PB - American Chemical Society (ACS)
SP - 2143-2151
IS - 5
VL - 141
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2019_Goncharova,
author = {Kseniia P Silaeva and Ashot V Arzumanyan and Roman G. Novikov and Pavel N. Solyev and Aziz M. Muzafarov and Irina K Goncharova and Anton A. Anisimov and Sergey A Milenin and Yaroslav V. Tkachev and Alexander D Volodin and Alexander Korlyukov},
title = {Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials},
journal = {Journal of the American Chemical Society},
year = {2019},
volume = {141},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021%2Fjacs.8b12600},
number = {5},
pages = {2143--2151},
doi = {10.1021/jacs.8b12600}
}
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Goncharova, Irina K., et al. “Aerobic Co-/N-Hydroxysuccinimide-Catalyzed Oxidation of p-Tolylsiloxanes to p-Carboxyphenylsiloxanes: Synthesis of Functionalized Siloxanes as Promising Building Blocks for Siloxane-Based Materials.” Journal of the American Chemical Society, vol. 141, no. 5, Jan. 2019, pp. 2143-2151. https://doi.org/10.1021%2Fjacs.8b12600.