Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7971 - 7977

Published: Jan. 1, 2023

Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C–H alkylation of N -heteroaromatics.

Language: Английский

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Regioselective Hydro(deutero)silylation of 1,3-Enynes Enabled by Photoredox/Nickel Dual Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 536 - 541

Published: Jan. 5, 2024

In the presence of visible light irradiation, organophoto/nickel dual catalysts, and mild base K2HPO4, 1,3-enynes react with silanecarboxylic acids to give corresponding α-silylallenes high selectivity. this uniquely decarboxylative hydrosilylation 1,3-enynes, a silyl radical process is involved diverse electron-rich -poor substrates proceed smoothly in moderate excellent yields. This transformation particularly synthetically worthwhile when using MeOD as solvent, which furnishes new access α-silyldeuteroallenes.

Language: Английский

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Visible light catalyzed arylsilylation of alkenes to construct silicon-containing 1,1-diaryl moieties

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4785 - 4791

Published: Jan. 1, 2024

We have developed an efficient photocatalyzed arylsilylation of alkenes, utilizing silylboranes and (hetero)aryl nitriles in the presence base photocatalyst.

Language: Английский

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Visible-Light-Mediated Deaminative Alkylation of Primary Amines with Silacarboxylic Acids via Isonitrile Formation

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 583 - 587

Published: Jan. 7, 2025

The functionalization of the C–N bond amines is a straightforward strategy for construction complex scaffolds or late-stage pharmaceuticals. Herein, we describe photoredox-catalyzed deaminative alkylation primary amine-derived isonitriles that provides unnatural amino acid derivatives under mild conditions. use silacarboxylic acids as silyl radical precursors enables generation carbon-centered radicals allow Csp3–Csp3 bonds via Giese-type addition, avoiding undesired hydrodeamination product.

Language: Английский

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C–H Bond Silylation of Heteroarenes

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3434 - 3453

Published: June 14, 2023

Abstract Organosilicon compounds are highly important molecular scaffolds with versatile synthetic utility, and used in a range of transformations. Such organosilicon employed wide research areas, including medicinal chemistry, drug discovery, pharmaceuticals, agrochemicals, fine chemicals, etc. Moreover, they commonly encountered number commercial products. However, the preparation by means traditional methods significantly limit their wider applications. Recently, several new concepts powerful have been developed order to prepare via transition-metal catalysis or without metal catalysis. While many procedures reported for silylation aromatic systems, heteroarenes scarce. Nevertheless excellent robust strategies heteroarene discovered. In this short review, we summarize different methods, mechanisms catalyst development regioselective heteroarenes. 1 Introduction 2 Silylation C–H Bonds through Organometallic Intermediates 2.1 Intermolecular Bond Assisted Directing Groups 2.2 Undirected 2.3 Intramolecular Tethered Silyl Unit 3 Silicon Electrophiles 4 Nucleophiles 5 Radicals 6 Other Approaches 6.1 Alkali-Metal-Catalyzed 6.2 Magnesium-Promoted Reductive 7 Conclusions Outlook

Language: Английский

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Photocatalyzed Deuterodichloromethylation of Olefins Using Silacarboxylic Acids as Halogen‐Atom Transfer Reagents

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

Published: March 7, 2025

Abstract A visible‐light‐induced deuterodichloromethylation of alkenes was developed with readily available and inexpensive deuterochloroform as the reagent. Silacarboxylic acids, which could generate silyl radicals through efficient decarboxylation, were applied halogen atom transfer agents. series deuterium‐containing gem ‐dichloroalkanes prepared in good yields.

Language: Английский

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Transition‐Metal‐Free Visible‐Light‐Induced Alkynylation of Silacarboxylic Acids

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(15)

Published: April 1, 2025

Abstract An operationally simple and mild protocol for the visible‐light‐induced intermolecular coupling of silacarboxylic acids with sulfonyl alkynes to form alkynylsilanes is presented. This study highlights use inexpensive readily available 4CzIPN as a photocatalyst, along more stable silyl radical precursors, enabling synthesis variety in good excellent yields, notably without need transition metals. The transformation offers several key advantages, including broad substrate scope, functional group tolerance, compatibility heterocyclic substrates. Furthermore, both scale‐up reaction late‐stage functionalization natural products have been successfully achieved under conditions. These features make process not only efficient but also versatile suitable wide range applications chemical modification.

Language: Английский

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Silver-catalyzed direct decarboxylative C H functionalization of azauracils with aliphatic carboxylic acids

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155619 - 155619

Published: April 1, 2025

Language: Английский

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Advances in Photoinduced Minisci-like Reactions

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract The Minisci reaction, which has been around for more than five decades, is still the preferred tool straightforward alkylation of basic heteroarenes. recent developments in photocatalysis have opened novel pathways radical generation under milder and sustainable conditions. Implementing this approach into reaction renewed interest transformation, attractive per se Medicinal Chemistry. Aspects such as sacrificial oxidants, catalysts, specific conditions should be carefully examined to evaluate practicability protocol. This short review focuses on advances (2020 February 2024) photoinduced Minisci-type reactions, emphasizing sustainability. 1 Introduction 2 Using Noble-Metal-Based Photocatalysts 3 Noble-Metal-Free Methods Sacrificial Oxidants 4 Without 5 Conclusions Perspectives

Language: Английский

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Metal-free photocatalyzed allylic silylation of allyl acetates and chlorides

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4836 - 4842

Published: Jan. 1, 2023

A visible light-induced organophotocatalytic strategy for synthesizing functionalized allylsilanes through radical allylic silylation of allyl acetates and chlorides is reported.

Language: Английский

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