Visible Light-Induced Reactions of Diazo Compounds and Their Precursors

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

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Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1393 - 1398

Published: Feb. 12, 2024

We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.

Language: Английский

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Metal- and photocatalyst-free three-component strategy to prepare benzylalcohol-, aldehyde-substituted BCP building blocks

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5531 - 5537

Published: Jan. 1, 2024

A mild one-step, light-promoted, three-component radical-coupling reaction of [1.1.1]propellane to afford difunctionalized benzylalcohol-, aldehyde-substituted BCPs in the absence metals, photocatalysts or external oxidants was reported.

Language: Английский

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Photocatalyzed 1,3-Bromodifluoroallylation of [1.1.1]Propellane with α-Trifluoromethylalkenes and KBr Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6889 - 6893

Published: Aug. 6, 2024

Herein we unveil a visible-light-driven transition-metal-free 1,3-bromodifluoroallylation of [1.1.1]propellane. This reactivity is harnessed through organophotocatalysis, providing practical synthetic pathways to 1-brominated-3-

Language: Английский

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Photochemical Tandem Reaction of Nitrogen Containing Heterocycles, Bicyclo[1.1.1]pentane, and Difluoroiodane(III) reagents

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(34), P. 7024 - 7034

Published: Jan. 1, 2024

A visible light-induced difluoroalkylation/heteroarylation of [1.1.1]propellane with nitrogen containing heterocycles and difluoroiodane(III) reagents was achieved. Various heteroarenes exhibited good compatibility, yielding the desired products in moderate to yields. The accessibility mild reaction conditions establish this method as an alternative practical strategy for accessing diverse 1-difluoroalkyl-3-heteroaryl bicyclo[1.1.1]pentanes (BCPs).

Language: Английский

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Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7026 - 7030

Published: Aug. 14, 2024

(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method light-induced, Cs

Language: Английский

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Site-Specific Radical Alkylation of Aryl Cyanide: Visible-Light, Photoredox-Catalyzed, Three-Component Arylalkylation of [1.1.1]Propellane

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7769 - 7773

Published: Sept. 4, 2024

We report herein a three-component radical arylalkylation of [1.1.1]propellane toward the synthesis aryl-substituted bicyclo[1.1.1]pentane derivatives. The use electron-deficient aryl cyanide as an group source not only reduces energy barrier arylation nucleophilic alkyl species, but also suppresses electrophilic Friedel-Crafts alkylation process, enabling present site-selective arylalkylation.

Language: Английский

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EDA Complex from BCP‐Thianthrenium Salt: A Catalyst‐free Strategy To Access 1‐Trifluoromethyl‐3‐quinoxaline Derivatives Bicyclo[1.1.1]pentanes

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 13, 2024

Abstract The construction of bicyclo[1.1.1.]pentanes (BCPs) typically require the cumbersome use labile [1.1.1.]propellane in solution and involve multicomponent radical reactions, which commonly produce undesired by‐products that hinder efficient BCPs. In this paper, we present a catalyst‐free strategy by constructing an electron donor‐acceptor (EDA) complex utilizing naturally electron‐deficient nature BCP thianthrenium salt, were irradiated with visible light to obtain trifluoromethyl‐BCP radicals through SET process, subsequently reacted various substituted quinoxalines. Moreover, successful structural modification drug molecule derivatives confirm utility scheme field discovery.

Language: Английский

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Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics^†

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Language: Английский

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Recent Advances in Radical Coupling Reactions Directly Involving Bicyclo[1.1.1]pentane (BCP)

Topics in Current Chemistry, Journal Year: 2025, Volume and Issue: 383(1)

Published: Jan. 18, 2025

Language: Английский

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