Iron-Catalyzed Photoinduced Remote C(sp³)–H Amination of Free Alcohols

Organic Letters, Journal Year: 2021, Volume and Issue: 23(22), P. 8968 - 8972

Published: Oct. 29, 2021

We report a general photocatalytic protocol for the remote C(sp3)-H bond amination of free aliphatic alcohols. The electron transfer between abundant and inexpensive catalyst FeCl3 simple alkanols under blue LED irradiation enables alkoxy radical formation mild redox-neutral conditions, with no need additional oxidant prefunctionalization. subsequent selective 1,5-hydrogen atom (HAT) provide efficient way to access molecular complexity from readily available bulk

Language: Английский

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When all C–C breaks LO–Ose

Trends in Chemistry, Journal Year: 2023, Volume and Issue: 5(3), P. 174 - 200

Published: Feb. 14, 2023

Organic peroxides are becoming popular intermediates for novel chemical transformations. The weak O-O bond is readily reduced by transition metals, including iron and copper, to initiate a radical cascade process that breaks C-C bonds. Great potential exists the rapid generation of complexity, originating from ability couple resulting free radicals with wide range partners. First, this review article discusses history synthesis organic peroxides, providing context necessary understand methodology. Then, it highlights 91 examples recent applications functionalization bonds accessed through metal-mediated reduction peroxides. Finally, we provide some comments about safety when working

Language: Английский

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Metal-free, visible-light driven C–H ketoalkylation of glycine derivatives and peptides

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(23), P. 9549 - 9553

Published: Jan. 1, 2021

A metal free, visible-light driven C–H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.

Language: Английский

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Copper-catalyzed alkylarylation of vinylarenes with cycloalkylsilyl peroxides and boronic acids

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(73), P. 10714 - 10717

Published: Jan. 1, 2020

A mild copper-catalyzed alkylarylation of vinylarenes with cycloalkylsilyl peroxides and boronic acids is described. This three-component protocol provides a straightforward approach to the remote keto-functionalized 1,1-diarylmethane derivatives. radical pathway initiated by C-C bond cleavage proposed for this tandem reaction.

Language: Английский

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Branching out: redox strategies towards the synthesis of acyclic α-tertiary ethers

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(14), P. 5878 - 5929

Published: Jan. 1, 2022

The synthesis of α-tertiary ethers has traditionally presented a major challenge; however, contemporary redox chemistry led to development plethora powerful new approaches.

Language: Английский

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Low‐Cost Transition Metal‐Catalyzed Heck‐Type Reactions: An Overview

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(7)

Published: Jan. 25, 2022

Abstract Heck coupling has emerged as an effective and powerful tool for C−C bond formations, with applications in academic industrial grounds. The conventional Mizoroki‐Heck reaction employed expensive Pd based catalysts, however, developments to meet low‐cost replacements is relevant from a sustainable point of view. Heck‐type couplings involving cost‐effective transition metals such Fe, Co, Ni, Cu have been established the recent decades. Herein, we comprehended metal‐catalyzed covering literature 2016.

Language: Английский

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The Formation of C–C or C–N Bonds via the Copper-Catalyzed Coupling of Alkylsilyl Peroxides and Organosilicon Compounds: A Route to Perfluoroalkylation

Organic Letters, Journal Year: 2021, Volume and Issue: 23(5), P. 1809 - 1813

Published: Feb. 24, 2021

The copper-catalyzed selective cleavage of alkylsilyl peroxides and the subsequent formation carbon–carbon or carbon–nitrogen bonds with organosilicon compounds are described. reaction proceeds under mild conditions exhibits a broad substrate scope respect to both cyclic acyclic in combination carbon nitrogen sources. In particular, this approach enables facile radical perfluoroalkylation using commercially available perfluoroalkyltrimethylsilanes. Our mechanistic studies suggest that should proceed via free-radical process.

Language: Английский

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Fe-Catalyzed Three-Component Coupling Reaction of α,β,γ,δ-Unsaturated Carbonyl Compounds and Conjugate Dienes with Alkylsilyl Peroxides and Nucleophiles

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(13), P. 8824 - 8834

Published: June 22, 2022

An Fe(OTf)2-catalyzed three-component coupling reaction of α,β,γ,δ-unsaturated carbonyl compounds with alkylsilyl peroxides in the presence certain heteronucleophiles (ROH and indole) is realized under mild conditions. A variety α,β,γ,δ-diene substrates different substituents were successfully employable via combination several peroxides. This new approach also applicable to double functionalization diene substrates.

Language: Английский

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Copper-catalyzed radical ring-opening halogenation with HX

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(69), P. 8652 - 8655

Published: Jan. 1, 2021

An efficient copper-catalyzed radical ring-opening halogenation with HX (aq) is described. This protocol provides a practical access to distally chlorinated, brominated and iodinated alkyl ketones nitriles moderate good yields.

Language: Английский

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Copper-catalyzed oxidative cyclization of 2-(1H-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-a]quinoxalines

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(12), P. 2370 - 2374

Published: Jan. 1, 2024

An efficient method was developed for the one-pot construction of pyrrolo[1,2- a ]quinoxalines via Cu( ii )-catalyzed domino reaction between 2-(1 H -pyrrol-1-yl)anilines and alkylsilyl peroxides.

Language: Английский

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