Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis DOI

Qi-Chao Shan,

Zhao Yan,

Yong Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 28, 2024

Language: Английский

Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters DOI Creative Commons
Ziying Wang, Shoujun Wang,

Nan‐Nan Dai

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 24, 2025

C–C bond cleavage and recombination provide an efficient strategy for the modification reconstruction of molecule structures. Herein, we present a method achieving amidation aryl C(sp2)–H through triple with involvement nitrous acid esters. This marks instance precise controlled stepwise bond, offering fresh perspective such bonds. Nitrous ester serves as both radical source hydrogen atom transfer (HAT) reagent to functionalize utilize two carbon atoms bond. The alkoxy captures from or N-hydroxyl induce 1,3-oxygen migration, which is crucial subsequent molecular authors report achieve bonds by participation

Language: Английский

Citations

5

Visible light/copper catalysis enabled Heck-like coupling between alkenes and cyclic sulfonium salts via selective C–S bond cleavage DOI

Xianqin Liu,

Xufeng Li, Linyuan Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(8), P. 2195 - 2200

Published: Jan. 1, 2024

A Heck-like coupling of cyclic sulfonium salts with alkenes via selective C–S bond cleavage using a copper complex as photosensitizer through visible-light-driven redox-neutral process has been developed.

Language: Английский

Citations

9

Efficient Low-Temperature catalytic depolymerization of LLDPE into valuable compounds using H-ZSM-5 catalysts and water DOI
Mei Ren, Jun Li, Manhong Huang

et al.

Fuel, Journal Year: 2024, Volume and Issue: 366, P. 131356 - 131356

Published: March 2, 2024

Language: Английский

Citations

5

Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis DOI

Hong-Jie Miao,

Jinhua Zhang, Shuai Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(30), P. 5563 - 5568

Published: July 21, 2023

A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation NH2 group onto 1,3-enyne moiety enabled further cyclization give unique scaffold containing lactone an indole moiety.

Language: Английский

Citations

13

Three-Component Reaction of Cyclopropanols, DABSO, and N-(Sulfonyl)acrylamides: Preparation of Sulfone-Bridged 1,7-Dicarbonyl Compounds DOI
Fei Chen, Li Xiao,

Ke-Ying Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7170 - 7175

Published: Aug. 19, 2024

A cascade reaction of cyclopropyl alcohols, DABSO (1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate), and N-(sulfonyl)acrylamides has been developed. This tandem process went through a cyclopropanol ring opening Michael addition sequence. The γ-keto sulfinate generated from the between serves as nucleophilic reagent, N-(sulfonyl)acrylamide is used acceptor. By utilizing this strategy, multitudinous sulfone-bridged 1,7-dicarbonyl compounds that contain both β-sulfonyl amide unit sulfone skeleton were conveniently synthesized.

Language: Английский

Citations

4

Visible-Light-Promoted C(sp3)–C(sp3) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination DOI
Kui‐Thong Tan,

Jiaan He,

Zhi-Lin Mu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(48), P. 8733 - 8738

Published: Nov. 22, 2023

A photoredox-catalyzed approach for the difluoroalkylation of amino acids was achieved through simultaneous decarboxylation and defluorination processes. This innovative protocol employs commonly available trifluoroacetophenones as primary starting materials, eliminating necessity preactivation. strategy has enabled synthesis several difluoroketone functionalized amines in moderate to impressive yields. These synthesized compounds are presented foundational molecules subsequent modification. The underlying mechanism transformation is anchored a single electron transfer (SET) radical pathway.

Language: Английский

Citations

8

Copper‐Catalyzed Asymmetric Radical 1,2‐Alkylesterification of 1,3‐Dienes with Cycloalkyl Hydroperoxides and Acids DOI
Tiantian Li, Ying Cheng, Wen‐Jing Xiao

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(23)

Published: Oct. 17, 2023

Abstract Transition‐metal‐catalyzed radical relay cross‐coupling reactions of 1,3‐dienes have recently emerged as one the most powerful methods for construction structurally diverse allylic compound in a single chemical step. However, there still has been limited success expanding substrate scope precursors and coupling partners, well exploring catalytic asymmetric variants. Herein, we report copper‐catalyzed enantioselective three‐component 1,2‐alkylesterification using cycloalkyl hydroperoxides carbonyl‐containing alkyl sources carboxylic acids O‐nucleophiles under mild redox‐neutral conditions. This protocol features broad good functional group tolerance with respect to each component, providing practical access variety distally keto‐functionalized esters high enantioselectivity. Mechanistic studies suggest involvement sequential C−O this reaction.

Language: Английский

Citations

6

Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of N-Functionalized Acrylamides DOI
Yingjie Ma,

Zi-Hang Yuan,

Pin Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9927 - 9940

Published: July 11, 2023

An array of redox-neutral alkylation/cyclization cascade reactions N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C-C bond cleavage. Through adjusting radical acceptors on N atom, a variety keto-alkylated chain-containing azaheterocycles, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines constructed by one-pot procedure good yields excellent functional group tolerance.

Language: Английский

Citations

4

Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis DOI

Qi-Chao Shan,

Zhao Yan,

Yong Wu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 28, 2024

Language: Английский

Citations

1