Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction

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Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction. / Ильин, Михаил Вячеславович ; Новиков, Александр Сергеевич ; Болотин, Дмитрий Сергеевич.

In: The Journal of organic chemistry, Vol. 87, No. 15, 05.08.2022, p. 10199-10207.

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

BibTeX

@article{5ef3f72275404b60ad118f583255ae3e,

title = "Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaym{\'e} Reaction",

abstract = "Sulfonium and selenonium salts, represented by S-aryl dibenzothiophenium and Se-aryl dibenzoselenophenium triflates, were found to exhibit remarkable catalytic activity in the model Groebke-Blackburn-Bienaym{\'e} reaction. Kinetic analysis and density functional theory (DFT) calculations indicated that their catalytic effect is induced by the ligation of the reaction substrates to the σ-holes on the S or Se atom of the cations. The experimental data indicated that although 10-fold excess of the chloride totally inhibits the catalytic activity of the sulfonium salts, the selenonium salt remains catalytically active, which can be explained by the experimentally found lower binding constant of the selenonium derivative to chloride in comparison with the sulfonium analogue. Both types of salts exhibit lower catalytic activity in the model reaction than dibenziodolium species.",

keywords = "Органокатализ, халькогенная связь, Механизм реакции",

author = "Ильин, {Михаил Вячеславович} and Новиков, {Александр Сергеевич} and Болотин, {Дмитрий Сергеевич}",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = aug,

day = "5",

doi = "10.1021/acs.joc.2c01141",

language = "English",

volume = "87",

pages = "10199--10207",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

RIS

TY - JOUR

T1 - Sulfonium and Selenonium Salts as Noncovalent Organocatalysts for the Multicomponent Groebke–Blackburn–Bienaymé Reaction

AU - Ильин, Михаил Вячеславович

AU - Новиков, Александр Сергеевич

AU - Болотин, Дмитрий Сергеевич

PY - 2022/8/5

Y1 - 2022/8/5

N2 - Sulfonium and selenonium salts, represented by S-aryl dibenzothiophenium and Se-aryl dibenzoselenophenium triflates, were found to exhibit remarkable catalytic activity in the model Groebke-Blackburn-Bienaymé reaction. Kinetic analysis and density functional theory (DFT) calculations indicated that their catalytic effect is induced by the ligation of the reaction substrates to the σ-holes on the S or Se atom of the cations. The experimental data indicated that although 10-fold excess of the chloride totally inhibits the catalytic activity of the sulfonium salts, the selenonium salt remains catalytically active, which can be explained by the experimentally found lower binding constant of the selenonium derivative to chloride in comparison with the sulfonium analogue. Both types of salts exhibit lower catalytic activity in the model reaction than dibenziodolium species.

AB - Sulfonium and selenonium salts, represented by S-aryl dibenzothiophenium and Se-aryl dibenzoselenophenium triflates, were found to exhibit remarkable catalytic activity in the model Groebke-Blackburn-Bienaymé reaction. Kinetic analysis and density functional theory (DFT) calculations indicated that their catalytic effect is induced by the ligation of the reaction substrates to the σ-holes on the S or Se atom of the cations. The experimental data indicated that although 10-fold excess of the chloride totally inhibits the catalytic activity of the sulfonium salts, the selenonium salt remains catalytically active, which can be explained by the experimentally found lower binding constant of the selenonium derivative to chloride in comparison with the sulfonium analogue. Both types of salts exhibit lower catalytic activity in the model reaction than dibenziodolium species.

KW - Органокатализ

KW - халькогенная связь

KW - Механизм реакции

UR - http://www.scopus.com/inward/record.url?scp=85136213453&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.2c01141

DO - 10.1021/acs.joc.2c01141

M3 - Article

VL - 87

SP - 10199

EP - 10207

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -

ID: 97253721