volume 24 issue 46 pages 8559-8563

Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane

Publication typeJournal Article
Publication date2022-11-09
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The removal of the tetrafluoropyridinyl group tethered to a sulfur atom using a complex of N-heterocyclic carbene (NHC) with borane is described. The reaction is performed under blue light irradiation with a disulfide as radical initiator. The selective cleavage of S-Ar in preference to the weaker S-Alk bond is achieved as a result of aromatic radical substitution of the thiyl group by a NHC-stabilized boron-centered radical. Alkyl thiols, which are the primary products of the dearylation, are in situ oxidized or alkylated, affording disulfides or sulfides, respectively.
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Panferova L. I. et al. Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane // Organic Letters. 2022. Vol. 24. No. 46. pp. 8559-8563.
GOST all authors (up to 50) Copy
Panferova L. I., Zubkov M. O., Kosobokov M. D., Dilman A. D. Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane // Organic Letters. 2022. Vol. 24. No. 46. pp. 8559-8563.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c03585
UR - https://doi.org/10.1021/acs.orglett.2c03585
TI - Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane
T2 - Organic Letters
AU - Panferova, Liubov I
AU - Zubkov, Mikhail O
AU - Kosobokov, Mikhail D
AU - Dilman, Alexander D
PY - 2022
DA - 2022/11/09
PB - American Chemical Society (ACS)
SP - 8559-8563
IS - 46
VL - 24
PMID - 36351082
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Panferova,
author = {Liubov I Panferova and Mikhail O Zubkov and Mikhail D Kosobokov and Alexander D Dilman},
title = {Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.orglett.2c03585},
number = {46},
pages = {8559--8563},
doi = {10.1021/acs.orglett.2c03585}
}
MLA
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MLA Copy
Panferova, Liubov I., et al. “Light-Promoted Dearylation of Perfluorinated Aryl Sulfides with N-Heterocyclic Carbene–Borane.” Organic Letters, vol. 24, no. 46, Nov. 2022, pp. 8559-8563. https://doi.org/10.1021/acs.orglett.2c03585.