Intermolecular Carbophosphination of Alkynes with Phosphole Oxides via Ni−Al Bimetal‐Catalyzed C−P Bond Activation DOI

Feng‐Ping Zhang,

Rong‐Hua Wang,

Jiang‐Fei Li

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(49)

Published: Oct. 17, 2023

Abstract Intermolecular carbophosphination reaction of alkynes or alkenes with unreactive C−P bonds remains an elusive challenge. Herein, we used a Ni−Al bimetallic catalyst to realize intermolecular 5‐membered phosphole oxides, providing series 7‐membered phosphepines in up 94 % yield.

Language: Английский

Recent advances in Pd-catalyzed asymmetric cyclization reactions DOI
Bing Xu,

Quanpu Wang,

Chao Fang

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 53(2), P. 883 - 971

Published: Dec. 18, 2023

This review aims to collect advancements in enantioselective palladium-catalyzed cyclization reactions over the past eleven years, and it is organized into thirteen sections depending on different types of transformations involved.

Language: Английский

Citations

41
Recent advances of Pd-π-allyl zwitterions in cycloaddition reactions DOI
Juan Du, Yunfan Li, Chang‐Hua Ding

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(11), P. 108401 - 108401

Published: March 30, 2023

Language: Английский

Citations

25
Lewis Acid-Catalyzed Benzannulation of Vinyloxiranes with 3-Formylchromones or 1,4-Quinones for Diversely Functionalized 2-Hydroxybenzophenones, 1,4-Naphthoquinones, and Anthraquinones DOI

Jihwan Gim,

Peter Yuosef M. Rubio,

Sonaimuthu Mohandoss

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2538 - 2549

Published: Feb. 1, 2024

A facile and convenient protocol for the regioselective construction of functionalized 2-hydroxybenzophenones is described. This involves Sc(OTf)3/BF3·OEt2-catalyzed benzannulation 2-vinyloxirans with 3-formylchromone, which cascade in situ diene formation, [4 + 2] cycloaddition, elimination, ring-opening strategies. Moreover, it provides an expedited synthetic pathway to access biologically intriguing 1,4-naphthoquinones anthraquinones including vitamin K3 tectoquinone. The synthesized compounds also hold potential use as UV filters show promise chemosensors Cu2+ Mg2+ ions.

Language: Английский

Citations

4
BF3·OEt2 Catalyzed Cascade [4 + 2] Benzannulation of Vinyloxiranes with Coumarins to Construct Benzocoumarin Derivatives DOI
Yafei Wang, Yujia Wang,

Jiaxin Qu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9462 - 9472

Published: June 13, 2024

A BF

Language: Английский

Citations

4
Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds DOI
Thomas P. Yang, Wei Du,

Chia‐Yu Wu

et al.

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

Published: Jan. 9, 2025

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3H)-furanone skeletons. The cycloaddition proceeds via 2(5H)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate phosphine catalysis. These findings highlight significant potential harnessing as versatile synthons constructing spirocyclic through simultaneous multicyclic skeleton formation.

Language: Английский

Citations

0
Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis DOI
Santosh K. Nanda

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11298 - 11319

Published: Jan. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Language: Английский

Citations

10
Palladium-Catalyzed (3 + 2) Annulation of Azaborines with Vinyl Epoxides for Constructing Polycyclic Oxazaborolidines DOI

Ziqi Zhu,

Ding-Hao Ge,

Zhijie Cao

et al.

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

Published: March 25, 2025

A palladium-catalyzed (3 + 2) annulation of azaborines with vinyl epoxides has been established. By this strategy, various polycyclic oxazaborolidines structural diversity were synthesized in generally high yields (up to 99%). The can be scaled up and the further functionalized through olefin metathesis Heck reaction, which demonstrated good feasibility for downstream transformations. Moreover, catalytic asymmetric version accomplished under catalysis palladium/chiral phosphoramidite ligand, producing chiral overall enantioselectivities 98:2 er). This work not only represents first 1,2-azaborines but also offers an efficient strategy constructing benzooxazaborolidine skeletons, particularly those enantioenriched fashion.

Language: Английский

Citations

0
Construction of nine-membered N,N,O-heterocycles via Pd-catalyzed [6+3] dipolar cycloaddition DOI

Hongling Xie,

Zhenkun Yang,

Luning Tang

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(75), P. 10560 - 10563

Published: Jan. 1, 2022

A new approach for the synthesis of 9-membered N,N,O-heterocycles by Pd-catalyzed [6+3] dipolar cycloaddition N-iminoisoquinolinium ylides and 2-vinyl oxetanes has been developed. The scope this was demonstrated with 28 examples. This is another important synthetic strategy medium-sized rings employing as ternary synthons.

Language: Английский

Citations

14
DMAP Catalyzed Ring-Opening/Cycloaddition of Vinyl Oxiranes with Activated Ketone Compounds to Construct the 1,3-Dioxolane Skeletons DOI

Jiaxin Qu,

Thomas P. Yang, Xin Zhao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9322 - 9327

Published: Oct. 24, 2024

The present work develops a DMAP-catalyzed [3 + 2] cycloaddition of vinyl oxiranes with activated ketone compounds, affording dioxolane derivatives moderate to excellent yields. This approach represents the first Lewis base (LB)-catalyzed ring-opening reaction epoxides, simultaneously providing rare oxygen-containing active intermediate in this field. gram-scale preparation and facile derivatization cycloadduct highlight significant synthetic potential strategy.

Language: Английский

Citations

2
Synthesis of Chiral 2,3-Dihydrofurans via One-Pot Pd-Catalyzed Asymmetric Allylic Cycloaddition and a Retro-Dieckmann Fragmentation Cascade DOI
Babar Hussain Shah, Sardaraz Khan, Can Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 12100 - 12104

Published: Aug. 8, 2023

An efficient method for the enantioselective synthesis of 2,3-dihydrofurans bearing a quaternary stereocenter has been developed via Pd-catalyzed asymmetric allylic cycloaddition and retro-Dieckmann Fragmentation cascade. The vinylethylene carbonates with 3-cyanochromone followed by base-assisted fragmentation proceeded smoothly one-pot process to produce chiral 3,4-disubstituted in high yields excellent enantioselectivities.

Language: Английский

Citations

6