Cu(II)-Catalyzed Annulative Sulfonylimination of α-Carbonyl-γ-alkynyl Sulfoxonium Ylides through Sulfoxonium Ylide Elimination for Access to (Z)-1H-Isochromenes

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1663 - 1670

Published: Jan. 21, 2025

1H-Isochromene scaffolds are ubiquitous in natural products and significant bioactive molecules. Although several methods for these molecular syntheses have been developed, reports on the efficient construction of iminated isochromenes still rather limited. Herein, we report a new Cu(II)-catalyzed annulation sulfonylimination cascade α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfamides, enabling direct C-C σ-bond elimination to furnish (Z)-1H-isochromenes 51-97% yields. During reaction process, ylide unit as traceless eliminative group is key successful sulfonylimination, which enables N-H insertion subsequent acetic acid-mediated elimination.

Language: Английский

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Transition-Metal-Catalyzed Directed C–H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3567 - 3567

Published: July 29, 2024

Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal migratory insertion processes. Among precursors, iodonium ylides serve as novel emerging precursor features including easy accessibility, thermal stability high activity, which have attracted great attention from organic chemists achieved tremendous success in transformation. In this review, recent progress on the application multifunctional coupling characteristics bond activation reactions is summarized, potential discussed.

Language: Английский

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Tunable Rh(III)-Catalyzed C(sp²)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7885 - 7890

Published: Sept. 6, 2024

A tunable Rh(III)-catalyzed C(sp

Language: Английский

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Synthesis of 2‐Pyrones by Base‐Induced [3+3] Annulation Reaction of Phenacyl Phosphonium Ylides with Cyclopropenones

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

Published: Oct. 18, 2024

Abstract The base‐induced [3+3] annulation reaction of phenacyl phosphonium ylides with cyclopropenones has been proposed. Various polysubstituted 2‐pyrones are achieved in moderate to good yields through C−P bond cleavage and C−O/C−C coupling under simple easy‐to‐operate conditions. synthetic application mechanism have also preliminarily explored gain a deeper understanding this strategy practicality details. This protocol offers an alternative approach for the synthesis useful 2‐pyrone derivatives.

Language: Английский

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Iron-Catalyzed Annulation of 2-Aminobenzaldehydes with Iodonium Ylides: A Mild and General Route for the Synthesis of Acridinone Derivatives

Asian Journal of Chemistry, Journal Year: 2024, Volume and Issue: 36(6), P. 1423 - 1428

Published: May 31, 2024

An inexpensive iron-catalyzed annulation of 2-aminobenzaldehydes with iodonium ylides for the synthesis acridinone derivatives was reported. A library biologically relevant 3,4-dihydropyridine-1-one scaffold synthesized by reaction corresponding 2-amino benzaldehyde and under mild conditions in a green solvent. The tolerates various alkyl, aryl halogenated substrates affords desired product moderate to good yields. reported has an catalytic system, conditions, easily accessible use solvents.

Language: Английский

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Rhodium-Catalyzed Synthesis of Phenanthrenes from Biarylboronic Acids and Sulfoxonium or Iodonium Ylides

Synfacts, Journal Year: 2024, Volume and Issue: 20(07), P. 0723 - 0723

Published: June 14, 2024

Key words rhodium catalysis - sulfoxonium ylides iodonium phenanthrenes

Language: Английский

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