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Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. / Kazantsev, Alexander; Rodionov, Ivan A.; Bakulina, Olga; Kantin, Grigory; Dar’in, Dmitry; Krasavin, Mikhail.

In: Catalysts, Vol. 13, No. 2, 428, 16.02.2023.

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

Harvard

Kazantsev, A, Rodionov, IA, Bakulina, O, Kantin, G, Dar’in, D & Krasavin, M 2023, 'Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran', Catalysts, vol. 13, no. 2, 428. https://doi.org/10.3390/catal13020428

APA

Kazantsev, A., Rodionov, I. A., Bakulina, O., Kantin, G., Dar’in, D., & Krasavin, M. (2023). Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. Catalysts, 13(2), [428]. https://doi.org/10.3390/catal13020428

Vancouver

Kazantsev A, Rodionov IA, Bakulina O, Kantin G, Dar’in D, Krasavin M. Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. Catalysts. 2023 Feb 16;13(2). 428. https://doi.org/10.3390/catal13020428

Author

Kazantsev, Alexander ; Rodionov, Ivan A. ; Bakulina, Olga ; Kantin, Grigory ; Dar’in, Dmitry ; Krasavin, Mikhail. / Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. In: Catalysts. 2023 ; Vol. 13, No. 2.

BibTeX

@article{df93beabf67e4fe8b8b0297bba4a9d38,
title = "Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran",
abstract = "(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones previously shown to yield two products in reactions with tetrahydrofuran mediated by rhodium carbenes—tetrahydrofur-2-yl-substituted product of C-H insertion and spirocyclic product of formal C-O insertion. Accidentally, it was noted that the ratio of the two products depends on the catalyst loading, and the phenomenon was investigated in detail. It was found to be of preparative significance: by solely changing the catalyst loading from 0.01 mol% to 10 mol%, one can obtain sound yields of either of the two products. Mechanistic and kinetic interpretation of this new phenomenon has been proposed.",
keywords = "α-diazocarbonyl compounds, diazo succinimides, rhodium catalyst, rhodium carbenes, C-H INSERTION, C-O insertion, catalyst loading, C-H insertion",
author = "Alexander Kazantsev and Rodionov, {Ivan A.} and Olga Bakulina and Grigory Kantin and Dmitry Dar{\textquoteright}in and Mikhail Krasavin",
note = "Kazantsev, A.; Rodionov, I.A.; Bakulina, O.; Kantin, G.; Dar{\textquoteright}in, D.; Krasavin, M. Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. Catalysts 2023, 13, 428. https://doi.org/10.3390/catal13020428",
year = "2023",
month = feb,
day = "16",
doi = "10.3390/catal13020428",
language = "English",
volume = "13",
journal = "Catalysts",
issn = "2073-4344",
publisher = "MDPI AG",
number = "2",

}

RIS

TY - JOUR

T1 - Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran

AU - Kazantsev, Alexander

AU - Rodionov, Ivan A.

AU - Bakulina, Olga

AU - Kantin, Grigory

AU - Dar’in, Dmitry

AU - Krasavin, Mikhail

N1 - Kazantsev, A.; Rodionov, I.A.; Bakulina, O.; Kantin, G.; Dar’in, D.; Krasavin, M. Catalyst Loading Controls Chemoselectivity: Unusual Effect in Rhodium(II) Carbene Insertion Reactions with Tetrahydrofuran. Catalysts 2023, 13, 428. https://doi.org/10.3390/catal13020428

PY - 2023/2/16

Y1 - 2023/2/16

N2 - (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones previously shown to yield two products in reactions with tetrahydrofuran mediated by rhodium carbenes—tetrahydrofur-2-yl-substituted product of C-H insertion and spirocyclic product of formal C-O insertion. Accidentally, it was noted that the ratio of the two products depends on the catalyst loading, and the phenomenon was investigated in detail. It was found to be of preparative significance: by solely changing the catalyst loading from 0.01 mol% to 10 mol%, one can obtain sound yields of either of the two products. Mechanistic and kinetic interpretation of this new phenomenon has been proposed.

AB - (E)-3-Arylidene-4-diazopyrrolidine-2,5-diones previously shown to yield two products in reactions with tetrahydrofuran mediated by rhodium carbenes—tetrahydrofur-2-yl-substituted product of C-H insertion and spirocyclic product of formal C-O insertion. Accidentally, it was noted that the ratio of the two products depends on the catalyst loading, and the phenomenon was investigated in detail. It was found to be of preparative significance: by solely changing the catalyst loading from 0.01 mol% to 10 mol%, one can obtain sound yields of either of the two products. Mechanistic and kinetic interpretation of this new phenomenon has been proposed.

KW - α-diazocarbonyl compounds

KW - diazo succinimides

KW - rhodium catalyst

KW - rhodium carbenes

KW - C-H INSERTION

KW - C-O insertion

KW - catalyst loading

KW - C-H insertion

UR - https://www.mendeley.com/catalogue/7dbf9ccf-d4c7-3e62-8d00-b14548045015/

U2 - 10.3390/catal13020428

DO - 10.3390/catal13020428

M3 - Article

VL - 13

JO - Catalysts

JF - Catalysts

SN - 2073-4344

IS - 2

M1 - 428

ER -

ID: 103050484