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Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone

Jie Zhang 1
Jie Zhang
, 
Yuhong Chen 1
Yuhong Chen
, 
Xiaohui Luo 1
Xiaohui Luo
, 
Zhengru Wen 1
Zhengru Wen
1 College of Pharmaceutics, Jinhua Polytechnic, Jinhua, P.R. China
10.1016/j.mencom.2022.03.034
Published 2022-03-06
Communication , Volume 32, Issue 2, 256-257
2
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Zhang J. et al. Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 256-257.
GOST all authors (up to 50) Copy
Zhang J., Chen Y., Luo X., Wen Z. Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 256-257.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.034
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.034
TI - Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone
T2 - Mendeleev Communications
AU - Zhang, Jie
AU - Chen, Yuhong
AU - Luo, Xiaohui
AU - Wen, Zhengru
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 256-257
IS - 2
VL - 32
ER -
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@article{2022_Zhang,
author = {Jie Zhang and Yuhong Chen and Xiaohui Luo and Zhengru Wen},
title = {Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.034},
number = {2},
pages = {256--257},
doi = {10.1016/j.mencom.2022.03.034}
}
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MLA Copy
Zhang, Jie, et al. “Rhodium-catalyzed regioselective cross-coupling of styrene oxides with arylboronic acids in aqueous γ-valerolactone.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 256-257. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.034.
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Keywords

arylboronic acids
green solvent
regioselectivity
Rhodium catalysis
styrene oxides
γ-valerolactone

Abstract

A simple and regioselective cross-coupling of styrene oxides with arylboronic acids in the presence of Rh(PPh3)3Cl in biomass-derived γ-valerolactone has been developed. The reactions proceeded smoothly to give 1,2-diaryl ethanols as the predominant products in moderate to good yields.

References

3.
Development of a Robust Procedure for the Copper-catalyzed Ring-Opening of Epoxides with Grignard Reagents
Alam M., Wise C., Baxter C.A., Cleator E., Walkinshaw A.
Organic Process Research and Development, 2012
5.
Cobalt-Mediated Mizoroki-Heck-Type Reaction of Epoxide with Styrene
Ikeda Y., Yorimitsu H., Shinokubo H., Oshima K.
Advanced Synthesis and Catalysis, 2004
9.
Pd‐Mediated Reactions of Epoxides
Muzart J.
European Journal of Organic Chemistry, 2011
10.
Nickel-Catalyzed Cross-Coupling of Styrenyl Epoxides with Boronic Acids
Nielsen D.K., Doyle A.G.
Angewandte Chemie - International Edition, 2011
12.
Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
Lu X., Yang C., Liu J., Zhang Z., Lu X., Lou X., Xiao B., Fu Y.
Chemical Communications, 2015
13.
Enantioselective Cross-Coupling of meso-Epoxides with Aryl Halides
Zhao Y., Weix D.J.
Journal of the American Chemical Society, 2015
14.
Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides
Potrząsaj A., Musiejuk M., Chaładaj W., Giedyk M., Gryko D.
Journal of the American Chemical Society, 2021
17.
Mechanism of Titanocene-Mediated Epoxide Opening through Homolytic Substitution
Gansäuer A., Barchuk A., Keller F., Schmitt M., Grimme S., Gerenkamp M., Mück-Lichtenfeld C., Daasbjerg K., Svith H.
Journal of the American Chemical Society, 2007
18.
Biomass-Derived Solvents for Sustainable Transition Metal-Catalyzed C–H Activation
Gandeepan P., Kaplaneris N., Santoro S., Vaccaro L., Ackermann L.
ACS Sustainable Chemistry and Engineering, 2019
19.
Selective rearrangement of terminal epoxides into methylketones catalysed by a nucleophilic rhodium–NHC–pincer complex
Jürgens E., Wucher B., Rominger F., Törnroos K.W., Kunz D.
Chemical Communications, 2015
20.
Peracid Reactions. III.1 The Oxidation of Bicyclo [2.2.1]heptadiene2
Meinwald J., Labana S.S., Chadha M.S.
Journal of the American Chemical Society, 1963