Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols
Publication type: Journal Article
Publication date: 2022-03-01
scimago Q1
wos Q2
SJR: 0.878
CiteScore: 7.2
Impact factor: 4.9
ISSN: 24688231
Catalysis
Physical and Theoretical Chemistry
Process Chemistry and Technology
Abstract
• The procedure for preparation of aryldifluoroboranes in solution was elaborated. • The measurement of the Lewis acidity of ArBF 2 showed that they are strong Lewis. • Aryldifluoroboranes catalyze the alkylation of phenols with styrene. • The linear correlation between Lewis acidity and the rate of alkylation was found. A series of aryldifluoroboranes was tested as homogeneous catalysts. The Lewis acidity of different ArBF 2 was determined by the Gutmann-Beckett method. A simple linear correlation was found between the Lewis acidity of ArBF 2 and the rate of phenol alkylation with styrene. Unexpected acceleration of alkylation of 4-XC 6 H 4 OH was observed in the series of X = OMe < tert -Bu < H < Br. The possible mechanism of catalysis with ArBF 2 including their primary coordination with oxygen atom and the further protonation of styrene with the formed oxonium complex was proposed.
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Shmakov M. M. et al. Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols // Molecular Catalysis. 2022. Vol. 521. p. 112202.
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Shmakov M. M., Prikhod'ko S. A., Peshkov R. Y., Bardin V. V., Adonin N. Y. Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols // Molecular Catalysis. 2022. Vol. 521. p. 112202.
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TY - JOUR
DO - 10.1016/j.mcat.2022.112202
UR - https://doi.org/10.1016/j.mcat.2022.112202
TI - Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols
T2 - Molecular Catalysis
AU - Shmakov, M M
AU - Prikhod'ko, S A
AU - Peshkov, R Y
AU - Bardin, V V
AU - Adonin, N Y
PY - 2022
DA - 2022/03/01
PB - Elsevier
SP - 112202
VL - 521
SN - 2468-8231
ER -
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@article{2022_Shmakov,
author = {M M Shmakov and S A Prikhod'ko and R Y Peshkov and V V Bardin and N Y Adonin},
title = {Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols},
journal = {Molecular Catalysis},
year = {2022},
volume = {521},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.mcat.2022.112202},
pages = {112202},
doi = {10.1016/j.mcat.2022.112202}
}
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