Synthesis of Indolyl-Tethered Spiro[cyclobutane-1,1′-indenes] through Cascade Reactions of 1-(Pyridin-2-yl)-1H-indoles with Alkynyl Cyclobutanols

Organic Letters, Год журнала: 2021, Номер 23(21), С. 8510 - 8515

Опубликована: Окт. 15, 2021

Presented herein is an efficient and unprecedented synthesis of indolyl-tethered spiro[cyclobutane-1,1'-indenes] through the cascade reaction 1-(pyridin-2-yl)-1H-indoles with alkynyl cyclobutanols. Mechanistic experiments implicate a sequential process in which 1-(pyridin-2-yl)-1H-indole first undergoes alkenylation cyclobutanol followed by intramolecular Friedel-Crafts to give title products. The utility this novel protocol was reflected ample substrate scope, high chemo- regioselectivity, removable directing group, scalable preparation. In addition, product thus obtained can be further derivatized quite efficiently.

Язык: Английский

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Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

ChemistrySelect, Год журнала: 2023, Номер 8(6)

Опубликована: Фев. 8, 2023

Abstract This review aims to collect and analyze recent results with respect the use of varied palladium preparations in synthesis five‐membered nitrogen heterocycles including condensed derivatives. Results have been selected focus on studies last three years. Furthermore, a common feature all methods treated here is that nitrogen‐containing ring formed via closing appropriate starting materials. Selected examples discussed will reveal plethora products from small monocycles multi‐ring systems can be successfully accessed. Major features are wide product ranges, high yields stereoselectivities often achieved under mild reaction conditions.

Язык: Английский

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Copper-catalyzed [1,3]-nitrogen rearrangement ofO-aryl ketoximesviaoxidative addition of N–O bond in inverse electron flow

Chemical Science, Год журнала: 2023, Номер 14(21), С. 5705 - 5711

Опубликована: Янв. 1, 2023

[1,3]-Nitrogen rearrangement reactions of O -aryl ketoximes was catalytically promoted by IPrCuBr and BF 3 ·OEt 2 . The oxidative addition the N–O bond to Cu catalyst is accelerated donation electrons from both nitrogen oxygen atoms.

Язык: Английский

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Copper-Catalyzed Synthesis of Furan-Tethered Benzocyclobutenes via Carbene-Mediated 1,4-Sulfinate Migration-Annulation

Organic Letters, Год журнала: 2024, Номер 26(26), С. 5453 - 5457

Опубликована: Июнь 24, 2024

A copper-catalyzed intramolecular cascade reaction of conjugated enynones has been achieved via a pivotal 1,4-sulfinate migration step. This process leverages cost-effective and ecofriendly copper salt as catalyst, enabling the efficient construction five- four-membered rings in rapid, sequential manner, producing furan-tethered benzocyclobutenes good to excellent yields under mild conditions. The is characterized by 100% atom economy, outstanding efficiency, diastereoselectivity cases studied. robustness this method evidenced its compatibility with air exposure use undistilled, commercially available solvents, further enhancing practicality.

Язык: Английский

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Pd(II)‐Catalyzed Asymmetric [2+2] Annulation for the Construction of Chiral Benzocyclobutenes

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 1, 2024

Asymmetric de novo synthesis of benzocyclobutenes (BCBs) via catalytic intermolecular reaction is highly desired for efficient access to this important class compounds, yet such a strategy remains unmet challenge. Here, we report Pd/Pyrox-catalyzed asymmetric [2+2] annulation between arylboronic acids and functionalized alkenes, providing an unprecedented protocol various enantio-enriched BCBs in modular versatile manner under mild conditions. A broad substrate scope with excellent enantioselectivity has been achieved the current protocol. The isolation characterization key chiral palladacycle intermediate, together DFT calculations, provides strong evidence pathway including enantiodetermining arylpalladation step.

Язык: Английский

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