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

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

3

Diversified Synthesis of Chiral Fluorinated Cyclobutane Derivatives Enabled by Regio‐ and Enantioselective Hydroboration DOI

Fushan Yuan,

Xingyu Qi,

Yuanyue Zhao

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)

Published: April 2, 2024

The diversified synthesis of chiral fluorinated cyclobutane derivatives has remained a difficult task in synthetic chemistry. Herein, we present an approach for asymmetric hydroboration and formal hydrodefluorination gem-difluorinated cyclobutenes through rhodium catalysis, providing α-boryl cyclobutanes monofluorinated with excellent regio- enantioselectivity, respectively. key to the success two transformations relies on efficient, mild highly selective rhodium-catalyzed HBPin (pinacolborane), which subsequent addition base, catalytic amount palladium some cases, results formation products four-membered ring retained. obtained are versatile building blocks that provide platform enantioenriched great diversity.

Language: Английский

Citations

12

Observation of unusual outer-sphere mechanism using simple alkenes as nucleophiles in allylation chemistry DOI Creative Commons
Yaxin Zeng, Han Gao, Zhong‐Tao Jiang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 21, 2024

Abstract Transition-metal catalyzed allylic substitution reactions of alkenes are among the most efficient methods for synthesizing diene compounds, driven by inherent preference an inner-sphere mechanism. Here, we present a demonstration outer-sphere mechanism in Rh-catalyzed reaction simple using gem -difluorinated cyclopropanes as allyl surrogates. This unconventional offers opportunity fluorine recycling via C − F bond cleavage/reformation, ultimately delivering carbofluorination products. The developed method tolerates wide range alkenes, providing access to secondary, tertiary fluorides and -difluorides with 100% atom economy. DFT calculations reveal that formation goes through unusual nucleophilic allyl-Rh species instead migration insertion, generated carbon cation then forms tetrafluoroborate fluoride shuttle.

Language: Английский

Citations

12

Palladium/Amine Dual-Catalyzed Tsuji–Trost Fluoroallylation of Aldehydes with gem-Difluorinated Cyclopropanes DOI
Zhengquan Su,

Binhong Tan,

Zhaodong Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5375 - 5379

Published: June 12, 2024

We herein disclose the Pd/amine dual-catalyzed ring-opening cross-coupling reaction between

Language: Английский

Citations

6

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

6

Synergistic Pd/Ni Dual-Catalyzed Cross-Coupling of Azaaryl Acetates with gem-Difluorinated Cyclopropanes DOI
Xuexue Zhang,

H. HELEN LIN,

Binhong Tan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8956 - 8960

Published: Oct. 7, 2024

We herein report the development of a novel Pd/Ni dual-catalyzed ring-opening functionalization

Language: Английский

Citations

6

Palladium-Catalyzed Regioselective Monofluoroallylation of Indoles with gem-Difluorocyclopropanes DOI
Zhenjie Wang, Chuang Liu, Junhai Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6905 - 6909

Published: Aug. 1, 2024

We present a palladium-catalyzed ring-opening reaction that induces indoles to cross-couple with gem-difluorocyclopropanes. The proceeds through domino process of C–C bond activation and C–F elimination, followed by C–C(sp2) coupling produce various 2-fluoroallylindoles. This method is characterized its high functional group tolerance, good yields regioselectivity, under base-free conditions. synthetic utility the products illustrated functionalization NH C2 positions indole scaffold.

Language: Английский

Citations

5

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 cross-coupling of gem-difluorocyclopropanes with gem-diborylalkanes: facile synthesis of a diverse array of gem-diboryl-substituted fluorinated alkenes DOI Creative Commons
Ebrahim‐Alkhalil M. A. Ahmed,

Hongchen Zhang,

Wen-Gen Cao

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(13), P. 10265 - 10272

Published: Jan. 1, 2025

This study introduces an efficacious palladium-catalyzed method for the regioselective and stereoselective cross-coupling of gem -difluorinated cyclopropanes with array -diborylalkanes under mild reaction conditions.

Language: Английский

Citations

0