Fluoro-Promoted Thermal Ring Expansion of Cyclopropyl Carbenes to gem-Difluorinated Cyclobutenes DOI

Xingyu Qi,

Fushan Yuan,

Xufei Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(48), P. 10317 - 10321

Published: Nov. 21, 2024

Synthesis of

Language: Английский

Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols with gem-Difluorinated Cyclopropanes DOI
Ziqi Yang,

Yiliang Gong,

Qing Gu

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4287 - 4293

Published: Feb. 25, 2025

Language: Английский

Citations

1
Double strain-release enables formal C–O/C–F and C–N/C–F ring-opening metathesis DOI Creative Commons

Yulei Zhu,

Jie Jia,

Xiangyu Song

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13800 - 13806

Published: Jan. 1, 2024

Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved double-bond metathesis, like olefin metathesis and carbonyl single-bond has received less attention the past decade. Herein, we describe first C(sp

Language: Английский

Citations

5
Intramolecular Fluoroacylation Enabled by TrBF4-Catalyzed Fluoride Recycling DOI

Alice A. Mcknight,

Yuriko H. Fujisato,

Namrata Khanal

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 27, 2025

Alkyne- and alkene-tethered acyl fluorides undergo intramolecular carbofluorination via fluoride recycling using catalytic TrBF4. Excellent stereoselectivity is observed for the alkyne addition, enabling access to novel fluorinated indan-2-ones (all ≥95:5 E/Z) cyclopentan-2-ones (85:15 E/Z). Fluorinated chroman-2-ones tertiary alkyl can also be synthesized this method, comparing favorably previously reported protocols that employ expensive metal catalysts under harsher conditions.

Language: Английский

Citations

0
Pd-IPent-Catalyzed Defluorinative Annulation of gem-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted N-H Pyrroles DOI
Wenhao Liu,

Yahui Ma,

Qiuwei Huang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 21, 2025

We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of gem-difluorocyclopropanes with enamides, which provides convenient and efficient strategy for the synthesis multisubstituted N-H pyrrole derivatives. This transformation selectively cleaves C1-C3 bond, two C-F bonds, C-N bond in one-pot procedure. Additionally, this protocol allows modification several bioactive molecules.

Language: Английский

Citations

0
Palladium-Catalyzed Dearomative Fluoroallylation of Pyrroles with gem-Difluorinated Cyclopropanes DOI
Long Gu, Fajie Duan,

Jiafeng Ye

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

We herein report the development of a novel Pd-catalyzed dearomative functionalization pyrroles with gem-difluorinated cyclopropanes (gem-F2CPs). This dearomative/ring-opening strategy streamlines diversity-oriented synthesis (DOS) α-quaternary 2-fluoroallylic 2H-pyrroles broad scope and excellent functional group tolerance, which enables efficient late-stage transformation complex bioactive molecule-derived gem-F2CPs. Derivation resulting fluoroallylic to different synthetically useful 2H-pyrrole motifs demonstrated synthetic value this methodology.

Language: Английский

Citations

0
Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes DOI

Zimin Wang,

Daniel C. Hong,

Hongfang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F cleavage. This regioselective features a broad substrate scope excellent functional group compatibility, affording variety linear 2-fluoroallylic scaffolds in good yields high Z-selectivity.

Language: Английский

Citations

0
Access to Vinyl gem‐Difluorinated Cyclopropanes via Photopromoted Palladium‐Catalyzed Heck Reaction DOI
Bin Li,

Quanxiang Feng,

Jingjing Yuan

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract A photopromoted Pd‐catalyzed Heck reaction of gem ‐difluorocyclopropyl bromides (DFCBs) with styrenes to deliver vinyl ‐difluorinated cyclopropanes (VDFCs) under mild conditions has been developed. The demonstrates good functional group compatibility while providing high E/Z ratio the products. Furthermore, desired VDFCs can be easily transformed into fluorinated cyclic/acyclic architectures, which may broaden its applications in organic synthesis.

Language: Английский

Citations

0
Recent advances in catalytic carbofluorination of unsaturated system via C−F bond reconstruction DOI Creative Commons
Yaxin Zeng, Xufei Yan, Ying Xia

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 12, P. 100109 - 100109

Published: Nov. 6, 2024

Language: Английский

Citations

0
Fluoro-Promoted Thermal Ring Expansion of Cyclopropyl Carbenes to gem-Difluorinated Cyclobutenes DOI

Xingyu Qi,

Fushan Yuan,

Xufei Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(48), P. 10317 - 10321

Published: Nov. 21, 2024

Synthesis of

Language: Английский

Citations

0