C–X (X = C, O, S, N, B, P) Bond Deuteration and Late‐Stage Applications DOI

Xu Hui,

Yun‐Qian Zhang, Hui‐Xiong Dai

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 7, 2024

Abstract Precise deuterium labeling has gained significant attentions owing to the wide applications in organic synthesis, medicinal chemistry, and materials. C−C C‐heteroatom bonds constitute skeleton of molecules. This review summarizes advancements on bond deuterations as well their late‐stage natural products pharmaceutically relevant

Language: Английский

Palladium‐Catalyzed Deuteration of Arylketone Oxime Ethers DOI
Zhenyu Wang, Xu Zhang, Wenqing Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(12)

Published: Jan. 27, 2024

We report herein the development of palladium-catalyzed deacylative deuteration arylketone oxime ethers. This protocol features excellent functional group tolerance, heterocyclic compatibility, and high deuterium incorporation levels. Regioselective some biologically important drugs natural products are showcased via Friedel-Crafts acylation subsequent deuteration. Vicinal meta-C-H bond functionalization (including fluorination, arylation, alkylation) para-C-H electro-rich arenes realized by using ketone as both directing leaving group, which is distinct from aryl halide in conventional dehalogenative

Language: Английский

Citations

3
Difluorocarbene-Enabled Dehydration of Primary Amides To Access Nitriles DOI

Bofan Feng,

Huosheng Guo,

Xiaosha Wang

et al.

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

Published: March 16, 2025

A cost-effective and environmentally friendly method for the direct conversion of primary amides to nitriles was developed using commercially available non-toxic ethyl bromodifluoroacetate as a difluorocarbene precursor under metal-free ligand-free conditions. The reaction features high yields tolerates various sensitive moieties, including alkyl, alkenyl, ether, sulfone, sulfoxide, heteroaryl, chloro, bromo, iodo, hydroxyl, nitro, cyano groups, late-stage modification complex molecules is also feasible. Moreover, present effective on large scales, showing potential industrial application.

Language: Английский

Citations

0
Gold(I)‐Catalyzed Synthesis of Benzofurans from Tetrahydropyranyl (THP) Ethers of o‐Alkynylphenols DOI

Jeremy W. Pisor,

Isabella Garcia, Kirubel T. Mamo

et al.

Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown

Published: May 9, 2025

Abstract The activation of π‐systems in alkenes and alkynes by homogeneous gold catalysts is a powerful tool for the synthesis benzo‐fused heterocycles. Decades development area catalysis have brought an array new with them discovery modes carbophilic alkynes, investigations previously unknown mechanistic pathways. In alignment these efforts, we report cyclization tetrahydropyranyl ethers 2‐alkynylphenols to form benzofurans catalyzed gold(I)–NHC complex. reaction proceeds efficiently at very low catalyst loadings, products good yields.

Language: Английский

Citations

0
Multisite modifications of arenes using ketones as removable handles enabled by Pd and norbornene cooperative catalysis DOI

Kailiang Tao,

Xing Wang, Huan Liu

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Language: Английский

Citations

3
Palladium‐Catalyzed Deuteration of Arylketone Oxime Ethers DOI
Zhenyu Wang, Xu Zhang, Wenqing Chen

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(12)

Published: Jan. 27, 2024

Abstract We report herein the development of palladium‐catalyzed deacylative deuteration arylketone oxime ethers. This protocol features excellent functional group tolerance, heterocyclic compatibility, and high deuterium incorporation levels. Regioselective some biologically important drugs natural products are showcased via Friedel–Crafts acylation subsequent deuteration. Vicinal meta ‐C−H bond functionalization (including fluorination, arylation, alkylation) para electro‐rich arenes realized by using ketone as both directing leaving group, which is distinct from aryl halide in conventional dehalogenative

Language: Английский

Citations

2
Nickel‐Catalyzed Reductive Coupling of Vinyl Triflates and 1,4‐Dicyanobenzene to Access Alkenyl Nitriles DOI
Lele Wang, Zhongxian Li, Jun Zhu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(3), P. 431 - 437

Published: Jan. 1, 2024

Abstract We report a vinyl cyanation reaction of triflates and readily available 1,4‐dicyanobenzene through nickel‐catalyzed reductive coupling process. The is operated under mild conditions with remarkable functional‐group compatibility. Cyclic various ring sizes substituents at different positions all reacted smoothly. synthetic utility demonstrated by the derivatization pharmaceutical natural compounds, scale‐up synthesis, functional group transformations. Preliminary mechanistic studies demonstrate that are more reactive than towards oxidative addition to nickel catalyst.

Language: Английский

Citations

1
Polyfluorinated benzoic acids as promising reagents for organic synthesis and medicinal chemistry DOI
Evgeny V. Shchegolkov, Yanina V. Burgart,

Irina V. Shchur

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(8), P. RCR5131 - RCR5131

Published: Aug. 1, 2024

Polyfluoroaromatic compounds occupy a special place in organic synthesis due to wide range of their chemical transformations and unique biological properties. The introduction the carboxyl function into polyfluoroarenes allows further diversification chemistry these compounds. This review summarizes data on polyfluorobenzoic acids, including derivatives polyfluorosalicylic acids. reactions esterification, amidation, reduction, decarboxylation, metal-catalyzed decarboxylative cross-coupling, C–H functionalization, reductive defluorination, nucleophilic aromatic substitution, heterocyclization complex formation are considered. Reactivity features polyfluorobenzoates comparison non-fluorinated counterparts highlighted. potential for practical applications acid derivatives, primarily as biologically active compounds, is presented. <br> Bibliography includes 300 references.

Language: Английский

Citations

1
Total Synthesis of Syringin and Its Natural Analogues via C—C Bond Activation of Aryl Ketones† DOI
Zhenyu Wang,

Yi Sun,

Guodong Sun

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3587 - 3592

Published: Aug. 24, 2023

Comprehensive Summary Syringin is found in the root of Acanthopanax senticosus (Rupr. Maxim.) Harms and belongs to lignin chemical compound with many biological activities. In this study, we employed commercially available starting materials accomplished total synthesis syringin 5 steps an overall yield 58%. Palladium‐catalyzed C(O)–C bond activation subsequent cross coupling reaction key construct its natural analogues.

Language: Английский

Citations

3
C–X (X = C, O, S, N, B, P) Bond Deuteration and Late‐Stage Applications DOI

Xu Hui,

Yun‐Qian Zhang, Hui‐Xiong Dai

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 7, 2024

Abstract Precise deuterium labeling has gained significant attentions owing to the wide applications in organic synthesis, medicinal chemistry, and materials. C−C C‐heteroatom bonds constitute skeleton of molecules. This review summarizes advancements on bond deuterations as well their late‐stage natural products pharmaceutically relevant

Language: Английский

Citations

0