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Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system

Andrei Nikolaevich Vedernikov 1
Andrei Nikolaevich Vedernikov
, 
Marat Damirovich Sayakhov 1
Marat Damirovich Sayakhov
, 
Boris Nikolaevich Solomonov 1
Boris Nikolaevich Solomonov
10.1070/MC1997v007n05ABEH000829
Published 1997-10-30
Communication , Volume 7, Issue 5, 205-206
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Vedernikov A. N., Sayakhov M. D., Solomonov B. N. Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system // Mendeleev Communications. 1997. Vol. 7. No. 5. pp. 205-206.
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Vedernikov A. N., Sayakhov M. D., Solomonov B. N. Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system // Mendeleev Communications. 1997. Vol. 7. No. 5. pp. 205-206.
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TY - JOUR
DO - 10.1070/MC1997v007n05ABEH000829
UR - https://mendcomm.colab.ws/publications/10.1070/MC1997v007n05ABEH000829
TI - Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system
T2 - Mendeleev Communications
AU - Vedernikov, Andrei Nikolaevich
AU - Sayakhov, Marat Damirovich
AU - Solomonov, Boris Nikolaevich
PY - 1997
DA - 1997/10/30
PB - Mendeleev Communications
SP - 205-206
IS - 5
VL - 7
ER -
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@article{1997_Vedernikov,
author = {Andrei Nikolaevich Vedernikov and Marat Damirovich Sayakhov and Boris Nikolaevich Solomonov},
title = {Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system},
journal = {Mendeleev Communications},
year = {1997},
volume = {7},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1997v007n05ABEH000829},
number = {5},
pages = {205--206},
doi = {10.1070/MC1997v007n05ABEH000829}
}
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Vedernikov, Andrei Nikolaevich, et al. “Mild alkane functionalisation leading to ethers: oxidative alkoxylation of cyclohexane with the dibromobis(phosphine)palladium(II)–sodium alkoxide system.” Mendeleev Communications, vol. 7, no. 5, Oct. 1997, pp. 205-206. https://mendcomm.colab.ws/publications/10.1070/MC1997v007n05ABEH000829.

Abstract

Dibromobis(phosphine)palladium(II) complexes, PdBr2(L)2 [L = PPh3, P(p-Tol)3], react with cyclohexane and an alcoholic solution of sodium alkoxide, NaOR (R = Me, Et, Pri), at 30–60°C affording the corresponding alkyl cyclohex-1-enyl ethers, ROC6H9, in 30–140% yield on palladium both under argon and under air; benzene is inert under the reaction conditions, sodium tert-butoxide does not enter the hydrocarbon alkoxylation.

References

1.
Thermal Activation of Alkane C–H Bonds by Palladium Catalysts. Carbonylation of Alkanes with Carbon Monoxide
Fujiwara Y., Takaki K., Watanabe J., Uchida Y., Taniguchi H.
Chemistry Letters, 1989
2.
Palladium(II) and/or copper(II)-catalyzed carboxylation of small alkanes such as methane and ethane with carbon monoxide
Nakata K., Yamaoka Y., Miyata T., Taniguchi Y., Takaki K., Fujiwara Y.
Journal of Organometallic Chemistry, 1994
3.
Carboxylation of Alkanes with Carbon Monoxide via Palladium-Catalyzed C-H Bond Activation.
TAKAKI K., NAKATA K., TANIGUCHI Y., FUJIWARA Y.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1994
5.
Alkane activation by homogeneous palladium complexes
Beattie J.K., Masters A.F., Sparkes M.L.
Applied Organometallic Chemistry, 1991
6.
10.1070/MC1997v007n05ABEH000829_bib4_2
Muzart
Comptes Rendu de l’Academie di Science, 1988
8.
Reversible thermal carbon–hydrogen bond cleavage in alkanes and arenes with dihalogenobis(triphenylphosphine)palladium(II) complexes
Vedernikov A.N., Kuramshin A.I., Solomonov B.N.
Journal of the Chemical Society Chemical Communications, 1994
9.
10.1070/MC1997v007n05ABEH000829_bib6_2
Vedernikov
Zh. Org. Khim., 1993
11.
10.1070/MC1997v007n05ABEH000829_bib8
Collman
Principles and Applications of Organotransition Metal Chemistry, 1987