volume 42 issue 8 pages 823-828

Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes

Shutao Qi 1
Yunkai Hua 1
Liangkai Pan 1
Junfeng Yang 1, 2
Junliang Zhang 1, 3
Publication typeJournal Article
Publication date2024-01-02
scimago Q1
wos Q2
SJR1.188
CiteScore9.4
Impact factor5.5
ISSN1001604X, 16147065
General Chemistry
Abstract
Comprehensive Summary

Herein, we report nickel‐catalyzed cross‐coupling of gem‐difluorinated cyclopropanes with boronic acids, providing the corresponding arylated 2‐fluoroallylic scaffolds. This approach used commercially available phosphine ligand Xantphos to obtain monofluorinated alkenes with high regioselectivity and Z‐stereoselectivity. Mechanistic studies proposed a Ni(II)‐fluoroallyl pathway and excluded the radical pathway. Meanwhile, DFT study of the reductive elimination clarified the origin of the high linear selectivity.

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GOST |
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GOST Copy
Qi S. et al. Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes // Chinese Journal of Chemistry. 2024. Vol. 42. No. 8. pp. 823-828.
GOST all authors (up to 50) Copy
Qi S., Hua Y., Pan L., Yang J., Zhang J. Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes // Chinese Journal of Chemistry. 2024. Vol. 42. No. 8. pp. 823-828.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/cjoc.202300579
UR - https://doi.org/10.1002/cjoc.202300579
TI - Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes
T2 - Chinese Journal of Chemistry
AU - Qi, Shutao
AU - Hua, Yunkai
AU - Pan, Liangkai
AU - Yang, Junfeng
AU - Zhang, Junliang
PY - 2024
DA - 2024/01/02
PB - Wiley
SP - 823-828
IS - 8
VL - 42
SN - 1001-604X
SN - 1614-7065
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Qi,
author = {Shutao Qi and Yunkai Hua and Liangkai Pan and Junfeng Yang and Junliang Zhang},
title = {Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes},
journal = {Chinese Journal of Chemistry},
year = {2024},
volume = {42},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/cjoc.202300579},
number = {8},
pages = {823--828},
doi = {10.1002/cjoc.202300579}
}
MLA
Cite this
MLA Copy
Qi, Shutao, et al. “Nickel‐Catalyzed Regio‐ and Stereoselective Defluorinative Arylation of gem‐Difluorinated Cyclopropanes.” Chinese Journal of Chemistry, vol. 42, no. 8, Jan. 2024, pp. 823-828. https://doi.org/10.1002/cjoc.202300579.