Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes DOI
Xinhua Zhang,

Zhi‐Hui Wang,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375

Published: June 7, 2024

Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.

Language: Английский

Ruthenium-catalysed direct C–H amidation of 4-aryl-pyrrolo[2,3-d]pyrimidines with acyl/phosphoryl azides DOI

Chenhong Pan,

Chun He,

Jiangrong Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1181 - 1185

Published: Jan. 1, 2024

A series of amidated and phosphoramidated pyrrolo[2,3- d ]pyrimidine derivatives were synthesized by Ru-catalysed direct C–H amidation using azides as amino sources in a mild, efficient highly site-selective manner.

Language: Английский

Citations

4
Copper-catalyzed the coupling reaction of sulfonylazides with formamides for the synthesis of N-sulfonyl amidines DOI

Guoyang Ma,

Xia Ran, Yawen Li

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 153, P. 133869 - 133869

Published: Feb. 2, 2024

Language: Английский

Citations

3
Insights into the mechanism of 3d transition-metal-catalyzed directed C(sp3)–H bond functionalization reactions DOI Creative Commons

Andrés García‐Viada,

Juan C. Carretero, Javier Adrio

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review provides an overview of the research advaces in Ni-, Cu-, Fe- and Co-catalyzed directed C(sp 3 )–H bond functionalization reactions; including design principles, mechanistic discussions, along with potential applications limitations.

Language: Английский

Citations

0
Catalytic Asymmetric Intramolecular Domino Allylic O-Alkylation/Allylic Dearomatization of Allyl Aryl Ethers DOI

Yun-Qiao Zhang,

Yinglong Li, Kun Wang

et al.

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

Published: June 2, 2025

An intramolecular asymmetric allylic O-alkylation/allylic dearomative spirocyclization cascade has been successfully developed with allyl aryl ethers. In the presence of palladium and a phosphoramidite ligand, series spirocyclohexadienones an exocyclic double bond were obtained in up to 98% yield ee. The alkylation mechanism was elucidated through control experiments. addition, scale-up reaction further transformations spirocyclic products also performed, demonstrating potential application this method.

Language: Английский

Citations

0
A Pd‐Catalyzed Annulation Strategy to Linearly Fused Functionalized N‐Heterocycles DOI Creative Commons
Larry Hoteite, Benjamin D. W. Allen,

Ms. Ergaiya A. Elhajj

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(21)

Published: Feb. 7, 2024

Linearly fused polycyclic piperidines represent common substructures in natural products and biologically active small molecules. We have devised a Pd-catalyzed annulation strategy to these compounds that converts readily available 2-tetralones indanones into scaffolds with the potential for control of both enantio- diastereoselectivity. Importantly, can be chemoselectively functionalized, providing an efficient robust methodology important nitrogen-containing

Language: Английский

Citations

1
Ir(iii)/Ag(i)-catalyzed directly C–H amidation of arenes with OH-free hydroxyamides as amidating agents DOI Creative Commons
Youpeng Zuo, Meijun Liu, Jun Du

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(9), P. 5975 - 5980

Published: Jan. 1, 2024

A versatile Ir( iii )-catalyzed C–H amidation of arenes by employing readily available and stable OH-free hydroxyamides as a novel source.

Language: Английский

Citations

0
Recent approaches for the synthesis of heterocycles from amidines via metal catalyzed C-H functionalization reaction DOI
Youpeng Zuo,

Pengfei Zuo,

Meijun Liu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5014 - 5031

Published: Jan. 1, 2024

Transition metal catalyzed C-H bond activation has become one of the most important tools for constructing new chemical bonds. Introducing directing groups to substrates is key a successful reaction, these can also be further transformed in reaction. Amidines with their unique structure and reactivity are ideal transition metal-catalyzed transformations. This review describes major advances mechanistic investigations activation/annulation tandem reactions amidines until early 2024, focusing on unsaturated compounds, such as alkynes, ketone, vinylene carbonate, cyclopropanols derivatives. Meanwhile this manuscript explores reaction different carbene precursors, example diazo azide, triazoles, pyriodotriazoles, sulfoxonium ylides well own activation/cyclization reactions. A bright outlook provided at end manuscript.

Language: Английский

Citations

0
Palladium-Catalyzed Cycloaddition Reactions of π–Allylpalladium 1,4-Dipoles with 1,3,5-Triazinanes: Access to Hexahydropyrimidines, 1,3-Oxazinanes, and 1,5-Diazocanes DOI
Xinhua Zhang,

Zhi‐Hui Wang,

Yan Chen

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8363 - 8375

Published: June 7, 2024

Palladium-catalyzed decarboxylation of 5-methylene-1,3-oxazinan-2-ones and 5-methylene-1,3-dioxan-2-ones to generate aza-π-allylpalladium oxa-π-allylpalladium 1,4-dipoles for [4 + 2] cycloaddition reaction with 1,3,5-triazinanes was developed, affording a wide range hexahydropyrimidine 1,3-oxazinane derivatives in good excellent yields (up 99%). The acyclic sulfonamido-substituted allylic carbonates as 1,4-dipole precursors also apply the developed synthesized strategy, achieving synthesis hexahydropyrimidines. Moreover, situ-generated undergoing dimeric 4] were demonstrated by construction 1,5-diazocane derivatives.

Language: Английский

Citations

0