Cited by Synthetic Versatility: The C-P Bond Odyssey

Rhodium‐Catalyzed Enantio‐ and Regioselective Allylation of Indoles with gem‐Difluorinated Cyclopropanes DOI

Hui Yang,

Yaxin Zeng,

Xiangyu Song

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)

Published: March 22, 2024

Abstract The use of gem ‐difluorinated cyclopropanes ( ‐DFCPs) as fluoroallyl surrogates under transition‐metal catalysis has drawn considerable attention recently but such reactions are restricted to producing achiral or racemic mono‐fluoroalkenes. Herein, we report the first enantioselective allylation indoles rhodium with ‐DFCPs. This reaction shows exceptional branched regioselectivity towards ‐DFCPs, which provides an efficient route enantioenriched fluoroallylated wide substrate scope and good functional group tolerance.

Language: Английский

Citations

Selectivity in Rh-catalysis with gem-difluorinated cyclopropanes DOI

Yaxin Zeng, Zhong‐Tao Jiang, Ying Xia

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(28), P. 3764 - 3773

Published: Jan. 1, 2024

This feature article summarizes our efforts towards developing Rh-catalyzed reactions of gem -difluorinated cyclopropanes, briefly discussing the design, selectivity, mechanisms and future research prospects.

Language: Английский

Citations

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

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

Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling DOI

Lulu Yang, Jiale Wu, Yang Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3208 - 3212

Published: April 10, 2024

Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R2PCl), which forms fragile C═N–O–PR2 species that undergoes N–O homolysis, fragmentation, and radical–radical coupling, leading to the formation cyano-containing phosphine oxides in good yields. The features an situ activation for radical generation, R2PCl plays dual role as both activator reactant.

Language: Английский

Citations

Palladium-catalyzed cross-coupling of gem-difluorocyclopropanes with gem-diborylalkanes: facile synthesis of a diverse array of gem-diboryl-substituted fluorinated alkenes DOI

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

Advances in catalysis using Xantphos-like ligands; simplicity goes a long way DOI

Piet W. N. M. van Leeuwen, Israel Cano, Zoraida Freixa

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 537, P. 216636 - 216636

Published: April 11, 2025

Language: Английский

Citations

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

Regio- and Diastereoselective Hydrophosphination and Hydroamidation of gem-Difluorocyclopropenes DOI

Yuanshuo Zhang,

Limei Tian, Yali Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5442 - 5457

Published: April 3, 2024

In this study, concise, efficient, and modular hydrophosphinylation hydroamidation of gem-difluorocyclopropenes were disclosed in a mild transition-metal-free pattern. Through approach, phosphorus, nitrogen-containing gem-difluorocyclopropanes produced moderate to good yields with excellent regio- diastereoselectivity. Readily available nucleophilic reagents, along inexpensive inorganic bases, employed. Multiple synthetic applications, including gram-scale derivatization reactions modification bioactive molecules, subsequently elaborated.

Language: Английский

Citations

Palladium-catalyzed (Z)-selective allylation of phosphine oxides with vinylethylene carbonates to construct phosphorus allyl alcohols DOI

Hua Huang, Yiqi Wu,

Luyao Han

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(15), P. 3068 - 3072

Published: Jan. 1, 2024

Allylphosphine oxide compounds are important building blocks with broad applications in organic synthesis and pharmaceutical science. Herein, we report an unprecedented palladium-catalyzed allylation of phosphine oxides vinylethylene carbonates, producing various phosphorus allyl alcohols excellent yields high

Language: Английский

Citations

Pd-Catalyzed Ring-Opening of gem-Difluorocyclopropanes for the Mono- and Bis-fluoroallylation of 1,3-Dicarbonyls DOI

Yuxuan Yan,

Wanqing Lu,

Huijun Qian

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1630 - 1630

Published: Jan. 1, 2024

Language: Английский

Citations