Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols

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Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols. / Shmakov, Mikhail M.; Prikhod'ko, Sergey A.; Peshkov, Roman Yu et al.

In: Molecular Catalysis, Vol. 521, 112202, 03.2022.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{9b0138b6f49048dc9f64fe61adbe1dc7,

title = "Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols",

abstract = "A series of aryldifluoroboranes was tested as homogeneous catalysts. The Lewis acidity of different ArBF2 was determined by the Gutmann-Beckett method. A simple linear correlation was found between the Lewis acidity of ArBF2 and the rate of phenol alkylation with styrene. Unexpected acceleration of alkylation of 4-XC6H4OH was observed in the series of X = OMe < tert-Bu < H < Br. The possible mechanism of catalysis with ArBF2 including their primary coordination with oxygen atom and the further protonation of styrene with the formed oxonium complex was proposed.",

keywords = "Alkylation, Aryldifluoroboranes, Gutmann-Beckett method, Lewis acidity, Organocatalysis",

author = "Shmakov, {Mikhail M.} and Prikhod'ko, {Sergey A.} and Peshkov, {Roman Yu} and Bardin, {Vadim V.} and Adonin, {Nicolay Yu}",

note = "Funding Information: Works on the development of approaches to the synthesis of aryldifluoroboranes containing one fluorine atom or other substituents in the aromatic ring as well as the catalytic and acidic properties study of aryldifluoroboranes were supported by research grant 19-43-543003 r_mol_a of Russian Foundation for Basic Research and the Ministry of Education of the Novosibirsk Region. Authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements. Funding Information: Works on the synthesis of polyfluoroaryldifluoroboranes and (polyfluoronaphthyl)difluoroborane as well as study of the mechanism of catalytic alkylation of aromatic compounds were supported by the Ministry of Science and Higher Education of the Russian Federation within the governmental order for Boreskov Institute of Catalysis (project АААА-А21-121011390055-8 ). Publisher Copyright: {\textcopyright} 2022",

year = "2022",

month = mar,

doi = "10.1016/j.mcat.2022.112202",

language = "English",

volume = "521",

journal = "Molecular Catalysis",

issn = "2468-8231",

publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Aryldifluoroboranes: Lewis acidity and catalytic activity in the alkylation of phenols

AU - Shmakov, Mikhail M.

AU - Prikhod'ko, Sergey A.

AU - Peshkov, Roman Yu

AU - Bardin, Vadim V.

AU - Adonin, Nicolay Yu

N1 - Funding Information: Works on the development of approaches to the synthesis of aryldifluoroboranes containing one fluorine atom or other substituents in the aromatic ring as well as the catalytic and acidic properties study of aryldifluoroboranes were supported by research grant 19-43-543003 r_mol_a of Russian Foundation for Basic Research and the Ministry of Education of the Novosibirsk Region. Authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements. Funding Information: Works on the synthesis of polyfluoroaryldifluoroboranes and (polyfluoronaphthyl)difluoroborane as well as study of the mechanism of catalytic alkylation of aromatic compounds were supported by the Ministry of Science and Higher Education of the Russian Federation within the governmental order for Boreskov Institute of Catalysis (project АААА-А21-121011390055-8 ). Publisher Copyright: © 2022

PY - 2022/3

Y1 - 2022/3

N2 - A series of aryldifluoroboranes was tested as homogeneous catalysts. The Lewis acidity of different ArBF2 was determined by the Gutmann-Beckett method. A simple linear correlation was found between the Lewis acidity of ArBF2 and the rate of phenol alkylation with styrene. Unexpected acceleration of alkylation of 4-XC6H4OH was observed in the series of X = OMe < tert-Bu < H < Br. The possible mechanism of catalysis with ArBF2 including their primary coordination with oxygen atom and the further protonation of styrene with the formed oxonium complex was proposed.

AB - A series of aryldifluoroboranes was tested as homogeneous catalysts. The Lewis acidity of different ArBF2 was determined by the Gutmann-Beckett method. A simple linear correlation was found between the Lewis acidity of ArBF2 and the rate of phenol alkylation with styrene. Unexpected acceleration of alkylation of 4-XC6H4OH was observed in the series of X = OMe < tert-Bu < H < Br. The possible mechanism of catalysis with ArBF2 including their primary coordination with oxygen atom and the further protonation of styrene with the formed oxonium complex was proposed.

KW - Alkylation

KW - Aryldifluoroboranes

KW - Gutmann-Beckett method

KW - Lewis acidity

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=85125306295&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/6a3567b6-c6e4-3c35-ba8f-8e446e75a617/

U2 - 10.1016/j.mcat.2022.112202

DO - 10.1016/j.mcat.2022.112202

M3 - Article

AN - SCOPUS:85125306295

VL - 521

JO - Molecular Catalysis

JF - Molecular Catalysis

SN - 2468-8231

M1 - 112202

ER -

ID: 35589249