Diversity‐Oriented Catalytic Asymmetric Dearomatization of Indoles with o‐Quinone Diimides

Advanced Science, Journal Year: 2023, Volume and Issue: 10(35)

Published: Oct. 23, 2023

Abstract Herein, the first diversity‐oriented catalytic asymmetric dearomatization of indoles with o ‐quinone diimides ( ‐QDIs) is reported. The (CADA) one research focuses in terms structural and biological importance dearomatized indole derivatives. Although great achievements have been made target‐oriented CADA reactions, reactions are regarded as more challenging remain elusive due to lack synthons featuring multiple reaction sites difficulty precise control chemo‐, regio‐, enantio‐selectivity. In this work, ‐QDIs employed a versatile building block, enabling chemo‐divergent dearomative arylation [4 + 2] cycloaddition indoles. Under catalysis chiral phosphoric acid mild conditions, various indolenines, furoindolines/pyrroloindolines, six‐membered‐ring fused indolines collectively prepared good yields excellent enantioselectivities. This synthesis protocol enriches chemistry offers new opportunities for reactions.

Language: Английский

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Catalytic Asymmetric Dearomative Arylation of 2‐Naphthols Enabled by o‐Quinone Diimides

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(20), P. 4238 - 4243

Published: March 16, 2024

Abstract The catalytic asymmetric dearomative arylation of 2‐naphthols enabled by the unconventional reactivity o ‐quinone diimides, i. e. 1,4‐conjugate addition on quinone sp 2 hybridized carbon, has been established. Under catalysis chiral phosphoric acid, various cyclohexaenones bearing an all‐carbon quaternary stereocenter have prepared with excellent yields and enantioselectivities.

Language: Английский

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Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 19, 2025

A novel [3+3] cyclization reaction between phenol and hydrazone was successfully developed under electrochemically driven conditions. This provided access to a diverse array of 1,3,4-oxadiazinane compounds in consistently high yields, reaching up 87%. Notably, the exhibited remarkable tolerance toward broad spectrum both substrates, underscoring its versatility. Moreover, protocol distinguished itself by exceptional atom step economy, facilitating efficient construction functionalized 1,3,4-oxadiazines. The synthetic utility this approach further exemplified scalability, as demonstrated gram-scale reactions, substrate scope.

Language: Английский

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Regioselective N-arylation of N-Acylsulfenamides Enabled by o-Quinone Diimides

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

Published: Feb. 27, 2025

The functionalization of N-acylsulfenamides is a research focus in organosulfur chemistry, as the N-S array has unique properties and versatile applications. Although great progress been made S-functionalization, N-functionalization, especially N-arylation N-acylsulfenamides, rarely explored because lower nucleophilicity N-site. Herein, we report Brønsted acid-catalyzed regioselective reaction with o-quinone diimides. Under mild metal-free conditions, wide range N-arylated have prepared good yields excellent regioselectivity. ease gram-scale synthesis transformations into useful sulfonamides demonstrates their synthetic practicality.

Language: Английский

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Synthesis of Carbazolylamines through Brønsted Acid‐Catalyzed Direct Electrophilic Aminations

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

Published: Aug. 21, 2024

Abstract A Brønsted acid catalyzed direct and dual C−H amination of carbazoles indolocarbazoles with N ‐Ts iminoquinone acetal is reported. It characterized that the mentioned was determined by selection catalysts molar ratio starting materials. The efficiency this protocol showcased diverse carbazolylamine indolocarbazolylamine assemblies. late‐stage functionalization a series natural products fully illustrates synthetic value methodology.

Language: Английский

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