Metal-free cascade O–H double insertion between I^(III)/S^(VI)-ylides, carboxylic acids, and alcohols: modular access to unsymmetrical α,α-O,O-substituted ketones

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3234 - 3241

Published: Jan. 1, 2024

Herein, we present a cascade O–H double insertion reaction between I (III) /S (VI) -ylides, carboxylic acids, and alcohols under metal-free conditions, enabling the modular synthesis of unsymmetrical α,α- O , -substituted ketones.

Language: Английский

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Rh(III)-catalyzed [4+1] annulation of sulfoxonium ylide with allyl alkyl ethers: A detailed theoretical study of DFT, anti-inflammatory and antidiabetic activity

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(36), P. 15989 - 15999

Published: Jan. 1, 2024

The [4+1] annulation of sulfoxonium ylides with allyl ether, catalyzed by Rh( iii ), efficiently produces alkyl-substituted indanone a broad substrate scope and excellent yield.

Language: Английский

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Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I^(III)/S^(VI) Ylides

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

Published: April 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Language: Английский

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Isocyanide-Based Multicomponent Reaction: Cascade α-Acyloxylation/Carboxamidation and [3 + 1+1] Cyclization of I^(III)/S^(VI)-Ylides

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6263 - 6268

Published: July 12, 2024

A metal-free cascade of α-acyloxylation/carboxamidation I(III)/S(VI)-ylides, carboxylic acids, and isonitriles via a Passerini-like multicomponent reaction is reported. Unexpectedly, [3 + 1+1] cyclization involving I(III)/S(VI)-ylides two molecules ethyl isocyanoacetate was observed. The strategy allows for the synthesis unsymmetrical α,α-disubstituted ketones functionalized pyrroles with up to 99% yield wide substrate compatibility. Notably, procedure has been extended late-stage modification drugs natural products, offering an elegant complement classic Passerini reaction.

Language: Английский

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Reactions with sulfoxonium ylides using metal-catalysis

Advances in organometallic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 227 - 286

Published: Jan. 1, 2024

Language: Английский

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