Aryldifluoroboranes: Lewis Acidity and Catalytic Activity in the Alkylation of Phenols
Full article
| Common |
Language:
Английский,
Genre:
Full article,
Status:
Published,
Source type:
Original
|
| Journal |
Molecular Catalysis
ISSN: 2468-8231
|
| Output data |
Year: 2022,
Volume: 521,
Article number
: 112202,
Pages count
: 6
DOI:
10.1016/j.mcat.2022.112202
|
| Tags |
Aryldifluoroboranes; Lewis acidity; Organocatalysis; Alkylation; Gutmann-Beckett method |
| Authors |
Shmakov Mikhail M.
1
,
Prikhod'ko Sergey A.
1
,
Peshkov Roman Yu
2
,
Bardin Vadim V.
3
,
Adonin Nicolay Yu
1
|
| Affiliations |
| 1 |
G.K. Boreskov Institute of Catalysis SB RAS, Lavrentiev Ave. 5, 630090 Novosibirsk, Russia
|
| 2 |
Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russia
|
| 3 |
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, 630090 Novosibirsk, Russia
|
|
Funding (2)
|
1
|
Russian Foundation for Basic Research
|
19-43-543003
|
|
2
|
Ministry of Science and Higher Education of the Russian Federation
|
0239-2021-0008
|
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.