Palladium‐Catalyzed Carbonylative Multicomponent Fluoroalkylation of 1,3‐Enynes: Concise Construction of Diverse Cyclic Compounds DOI Creative Commons
Chang‐Sheng Kuai,

Bing‐Hong Teng,

Xiao‐Feng Wu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(8)

Published: Dec. 20, 2023

Abstract Multicomponent reactions, particularly those entailing four or more reagents, have presented a longstanding challenge due to the inherent complexities associated with balancing reactivity, selectivity, and compatibility. In this study, we describe palladium‐catalyzed multi‐component fluoroalkylative carbonylation of 1,3‐enynes. A series products featuring three active functional groups‐allene, fluoroalkyl, carboxyl, were efficiently selectively integrated in single chemical operation. Furthermore, intricate fluoroalkyl‐substituted pyrimidinones can be constructed by simply altering 1,3‐bisnucleophilic reagent. This approach also provides valuable strategy for late‐stage modification naturally occurring molecules concise construction diverse cyclic compounds.

Language: Английский

Difluoroalkylative carbonylation of alkenes to access carbonyl difluoro-containing heterocycles: convenient synthesis of gemigliptin DOI Creative Commons
Zhipeng Bao, Youcan Zhang,

Le‐Cheng Wang

et al.

Science China Chemistry, Journal Year: 2022, Volume and Issue: 66(1), P. 139 - 146

Published: Dec. 12, 2022

Abstract Fluorinated heterocycles play a vital role in pharmaceutical and agrochemical industries. Hence, rapid efficient construction of fluorinated remains highly demanded. Herein, difluoroalkylative carbonylative cyclization unactivated alkenes ethylene gas enabled by palladium catalysis has been developed for the first time toward synthesis α-carbonyl difluoro-modified glutarimides. This procedure can also be applied to GeMigliptin which is medicine approved treatment type 2 diabetes mellitus.

Language: Английский

Citations

34
Palladium‐Catalyzed Carbonylative Multicomponent Fluoroalkylation of 1,3‐Enynes: Concise Construction of Diverse Cyclic Compounds DOI Creative Commons
Chang‐Sheng Kuai,

Bing‐Hong Teng,

Xiao‐Feng Wu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(8)

Published: Dec. 20, 2023

Multicomponent reactions, particularly those entailing four or more reagents, have presented a longstanding challenge due to the inherent complexities associated with balancing reactivity, selectivity, and compatibility. In this study, we describe palladium-catalyzed multi-component fluoroalkylative carbonylation of 1,3-enynes. A series products featuring three active functional groups-allene, fluoroalkyl, carboxyl, were efficiently selectively integrated in single chemical operation. Furthermore, intricate fluoroalkyl-substituted pyrimidinones can be constructed by simply altering 1,3-bisnucleophilic reagent. This approach also provides valuable strategy for late-stage modification naturally occurring molecules concise construction diverse cyclic compounds.

Language: Английский

Citations

19
Visible light induced four component reaction of styrene for the access of thiodifluoroesters DOI

Shaohui Yang,

Jingcheng Song,

Hao Yang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 34(9), P. 108131 - 108131

Published: Jan. 5, 2023

Language: Английский

Citations

18
Visible-Light-Mediated Bimetal-Catalyzed meta-Alkylation of Arenes DOI
Pengcheng Cui, Guan‐Wu Wang

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 427 - 432

Published: Jan. 8, 2024

A mild approach to the visible-light-mediated bimetal-catalyzed meta-alkylation of arenes has been accomplished. The regioselective is realized by a bimetallic ruthenium–palladium system. Ruthenium acts as catalyst for directing effect and photosensitizer, while cocatalyst palladium behaves generation fluoroalkyl radicals. This reaction not only suitable two-component meta-fluoroalkylation but can also be extended three-component reactions achieve bifunctionalization olefins.

Language: Английский

Citations

8
Palladium‐Catalyzed Direct Carbonylation of Bromoacetonitrile to Synthesize 2‐Cyano‐N‐acetamide and 2‐Cyanoacetate Compounds DOI Creative Commons
Zhipeng Bao, Xiao‐Feng Wu

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(19)

Published: March 14, 2023

Nitrile compounds containing ester and amide groups are important functionalized chemicals in synthetic medicinal chemistry. In this article, an efficient convenient palladium-catalyzed carbonylative procedure toward 2-cyano-N-acetamide 2-cyanoacetate has been developed. The reaction proceeds under mild conditions via radical intermediate which is suitable for late-stage functionalization. Gram-scale experiment was performed successfully low catalyst loading gave the target product excellent yield. Additionally, transformation can be atmospheric pressure provide alternative routes to 7 drug precursors.

Language: Английский

Citations

14
Carbonylative five-component synthesis of amides and esters with α-quaternary carbon center DOI
Zhipeng Bao,

Hefei Yang,

A Ru‐Han

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111150 - 111150

Published: March 1, 2025

Language: Английский

Citations

0
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

0
Visible-light-driven four-component diacylation of styrenes with acyl azolium salts: carbonylative synthesis of 1,4-diketones DOI
Maolin Yang, Yukun Liu, Peng Yang

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 21, 2025

Language: Английский

Citations

0
Single-Electron-Transfer-Mediated Carbonylation Reactions DOI Creative Commons

Le‐Cheng Wang,

Xiao‐Feng Wu

Accounts of Chemical Research, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

ConspectusTransition-metal-catalyzed carbonylation coupling methods have been accepted as an essential tool for producing carbonylated products over the past few decades. Despite its long-standing history and widespread industrial applications, several challenges remain in chemistry. These include reliance on precious metal catalysts, need of high-energy radiation, difficulties unactivated chemical bonds, etc. As alternative to classic two-electron transfer process, single-electron-transfer (SET)-mediated has emerged a powerful achieve elusive transformations. Over years, commonly available functional handles, such alkenes alkyl halides, via single-electron pathway valuable area research.Our team dedicated developing new reactions using bulk chemicals construct high-value products. broad synthetic motivating us explore SET-mediated transformations two key classes chemicals: alkanes halides. Specifically, our work centered main approaches: (1) Single-electron reduction C(sp3)-X bonds: this strategy leverages activate promoting formation carbon radicals, which turn promotes subsequent addition metals or CO. However, significant challenge lies highly negative potential certain substrates [Ered < -2 V compared saturated calomel electrode (SCE) iodides]. these challenges, intrinsic reducibility CO reactivity various carbonyl-metal intermediates facilitate smooth reaction progress. (2) oxidative C(sp3)-H emphasizes efficiency, high atomic utilization, minimal waste by bypassing traditional preactivation methods. Using 3d we successfully performed aminocarbonylation alkoxycarbonylation wide range bonds (such those aliphatic alkanes, ethers, amines, etc.). The above approaches also enabled radical relay alkenes, allowing precise control pathways. Such improves both efficiency selectivity. advancements transition photoredox catalysis resulting oxyalkylative carbonylation, aminoalkylative fluoroalkylative double rearrangement carbonylation.SET-mediated significantly enhances sustainability scalability process reducing catalysts enabling milder conditions. Additionally, carefully controlling intermediates, fine-tuned produce with This flexibility expands applications chemistry processes. Finally, place particular emphasis application drug discovery, where they serve handles late-stage modification bioactive molecules. applicability enriches toolbox synthesis, efficient functionalization complex versatile approach accelerate discovery novel therapeutic agents, making it critical modern medicinal

Language: Английский

Citations

0
Palladium-Catalyzed Hydroalkoxycarbonylation and Hydroxycarbonylation of Cyclopent-3-en-1-ols: Divergent Synthesis of Bridged Cyclic Lactones and β,γ-Unsaturated Carboxylic Acids DOI
Ming Chen, Yang Li, Zheng‐Hui Guan

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2571 - 2576

Published: April 6, 2023

Herein, we report a palladium-catalyzed hydroalkoxycarbonylation and hydroxycarbonylation of cyclopent-3-en-1-ols to form bridged bicyclic lactones β,γ-unsaturated carboxylic acid. The divergent reactivity is mainly tuned by the palladium catalyst ligands. reaction occurs additive-free has broad substrate scope. Several valuable synthetic medical intermediates are accessible through this protocol.

Language: Английский

Citations

9