Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen
Ivan A Yaremenko
1
,
Yulia Yu Belyakova
1
,
Arina A Demina
1
,
Peter S Radulov
1
,
Igor V. Alabugin
2
,
Publication type: Journal Article
Publication date: 2023-10-27
scimago Q1
wos Q1
SJR: 0.930
CiteScore: 8.0
Impact factor: 4.0
ISSN: 16154150, 16154169
Catalysis
Organic Chemistry
Abstract
A selective reaction of bridged ozonides with Fe(II) salts proceeds through the sequence of O−O, C−C scissions and halogenation to form α‐halogen substituted δ‐ketoesters and δ‐diketones in 15–72% yields. The overall sequence shows how a temporary installation of a peroxide functionality can be used to replace the acyl group within an acetoacetic ester unit with a halogen.
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Yaremenko I. A. et al. Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 23. pp. 4190-4197.
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Yaremenko I. A., Belyakova Y. Yu., Demina A. A., Radulov P. S., Alabugin I. V., Terent'ev A. O. Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen // Advanced Synthesis and Catalysis. 2023. Vol. 365. No. 23. pp. 4190-4197.
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TY - JOUR
DO - 10.1002/adsc.202300881
UR - https://doi.org/10.1002/adsc.202300881
TI - Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen
T2 - Advanced Synthesis and Catalysis
AU - Yaremenko, Ivan A
AU - Belyakova, Yulia Yu
AU - Demina, Arina A
AU - Radulov, Peter S
AU - Alabugin, Igor V.
AU - Terent'ev, Alexander O.
PY - 2023
DA - 2023/10/27
PB - Wiley
SP - 4190-4197
IS - 23
VL - 365
SN - 1615-4150
SN - 1615-4169
ER -
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BibTex (up to 50 authors)
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@article{2023_Yaremenko,
author = {Ivan A Yaremenko and Yulia Yu Belyakova and Arina A Demina and Peter S Radulov and Igor V. Alabugin and Alexander O. Terent'ev},
title = {Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen},
journal = {Advanced Synthesis and Catalysis},
year = {2023},
volume = {365},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/adsc.202300881},
number = {23},
pages = {4190--4197},
doi = {10.1002/adsc.202300881}
}
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MLA
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Yaremenko, Ivan A., et al. “Bioinspired Fe(II)‐mediated halogenative C‐C bond activation of ozonides: Temporary installment of a peroxide bridge allows selective C‐C scissions for replacement of a carbonyl group by a halogen.” Advanced Synthesis and Catalysis, vol. 365, no. 23, Oct. 2023, pp. 4190-4197. https://doi.org/10.1002/adsc.202300881.