Home / Publications / (XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes

(XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes

Maxim Alexandrovich Novikov 1
Maxim Alexandrovich Novikov
, 
Angelina Yu Bobrova 1
Angelina Yu Bobrova
, 
Anton Artemovich Servetnik 1
Anton Artemovich Servetnik
, 
Elena Ivanovna Chernoburova 1
Elena Ivanovna Chernoburova
, 
Igor Viktorovich Zavarzin 1
Igor Viktorovich Zavarzin
, 
10.1016/j.mencom.2024.09.023
Published 2024-09-09
Communication , Volume 34, Issue 5, 698-700
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Novikov M. A. et al. (XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 698-700.
GOST all authors (up to 50) Copy
Novikov M. A., Bobrova A. Yu., Servetnik A. A., Chernoburova E. I., Zavarzin I. V., Tomilov Y. V. (XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 698-700.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.09.023
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.023
TI - (XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes
T2 - Mendeleev Communications
AU - Novikov, Maxim Alexandrovich
AU - Bobrova, Angelina Yu
AU - Servetnik, Anton Artemovich
AU - Chernoburova, Elena Ivanovna
AU - Zavarzin, Igor Viktorovich
AU - Tomilov, Yury Vasil'evich
PY - 2024
DA - 2024/09/09
PB - Mendeleev Communications
SP - 698-700
IS - 5
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Novikov,
author = {Maxim Alexandrovich Novikov and Angelina Yu Bobrova and Anton Artemovich Servetnik and Elena Ivanovna Chernoburova and Igor Viktorovich Zavarzin and Yury Vasil'evich Tomilov},
title = {(XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.023},
number = {5},
pages = {698--700},
doi = {10.1016/j.mencom.2024.09.023}
}
MLA
Cite this
MLA Copy
Novikov, Maxim Alexandrovich, et al. “(XantPhos)AgBr as a cheap and readily available catalyst for the bromofluorocyclopropanation of electron-rich alkenes.” Mendeleev Communications, vol. 34, no. 5, Sep. 2024, pp. 698-700. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.023.

Keywords

alkenes
bromofluorocarbene
cyclopropanation
Cyclopropanes
organofluorine compounds
ozonolysis.
silver catalysis

Abstract

A silver phosphine complex (XantPhos)AgBr proved to be a cheap and readily accessible catalyst for bromofluoro- cyclopropanation of electron-rich alkenes with CFBr2CO2Na. Ozonolysis followed by treatment with NaHSO3 was shown to be an effective protocol to purify gem-bromofluoro- cyclopropanes from unreacted alkene precursors.

References

.
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds
Johnson B.M., Shu Y., Zhuo X., Meanwell N.A.
Journal of Medicinal Chemistry, 2020
.
Volchkov N.V., Novikov M.A., Lipkind M.B., Nefedov O.M.
Mendeleev Communications, 2013
.
Liquid–Liquid Extraction Protocol for the Removal of Aldehydes and Highly Reactive Ketones from Mixtures
Boucher M.M., Furigay M.H., Quach P.K., Brindle C.S.
Organic Process Research and Development, 2017
.
Pd-Catalyzed Regioselective Activation ofgem-Difluorinated Cyclopropanes: A Highly Efficient Approach to 2-Fluorinated Allylic Scaffolds
Xu J., Ahmed E., Xiao B., Lu Q., Wang Y., Yu C., Fu Y.
Angewandte Chemie - International Edition, 2015
.
Synthesis of Fluoro‐, Monofluoromethyl‐, Difluoromethyl‐, and Trifluoromethyl‐Substituted Three‐Membered Rings
Decaens J., Couve‐Bonnaire S., Charette A.B., Poisson T., Jubault P.
Chemistry - A European Journal, 2020
.
Catalytic asymmetric synthesis of monofluoroalkenes and gem-difluoroalkenes: advances and perspectives
Zhang X., Cheng Y., Zhao X., Cao Z., Xiao X., Xu Y.
Organic Chemistry Frontiers, 2021
.
Formation of a chiral 1-fluoro-2,2-diphenylcyclopropyl radical in the Barton decarboxylation reaction
Gawronska K., Gawronski J., Walborsky H.M.
Journal of Organic Chemistry, 1991
.
Substituent Effects in the Solvolysis ofp-(2-Substituted Cyclopropyl)-α-Methylbenzyl Chlorides
Kusuyama Y., Kubo T., Iyo M., Kagosaku T., Tokami K.
Bulletin of the Chemical Society of Japan, 1991
.
Yu. Bobrova A., Novikov M.A., Novikov R.A., Dorovatovskii P.V., Volodin A.D., Korlyukov A.A., Tomilov Y.V.
Mendeleev Communications, 2022
.
Syntheses and Applications of Monofluorinated Cyclopropanes
David E., Milanole G., Ivashkin P., Couve-Bonnaire S., Jubault P., Pannecoucke X.
Chemistry - A European Journal, 2012
.
Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
Novikov M.A., Ibatov Y.A., Volchkov N.V., Lipkind M.B., Semenov S.E., Nefedov O.M.
Journal of Fluorine Chemistry, 2017
.
Fluorine biocatalysis
Wu L., Maglangit F., Deng H.
Current Opinion in Chemical Biology, 2020
.
(NHC)AgCl catalyzed bromofluorocyclopropanation of alkenes with CFBr2CO2Na
Andrianova A.A., Maslova Y.D., Novikov M.A., Semenov S.E., Nefedov O.M.
Journal of Fluorine Chemistry, 2018
.
Synthesis of Monofluoroalkenes: A Leap Forward
Paquin J., Drouin M., Hamel J.
Synthesis, 2018
.
Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines
Kawanaka Y., Kobayashi K., Kusuda S., Tatsumi T., Murota M., Nishiyama T., Hisaichi K., Fujii A., Hirai K., Naka M., Komeno M., Odagaki Y., Nakai H., Toda M.
Bioorganic and Medicinal Chemistry, 2003
.
Regiodivergent Electroreductive Defluorinative Carboxylation of gem-Difluorocyclopropanes
Zhao B., Pan Z., Pan J., Deng H., Bu X., Ma M., Xue F.
Green Chemistry, 2023