An electrocatalytic mono-functionalization of alkenes towards alkenyl selenium sulfonates

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

In this study, a straightforward and environmentally benign electrochemical mono-functionalization of alkenes has been established for the synthesis alkenyl selenium sulfonates using elemental as source.

Language: Английский

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Divergent Synthesis of [3,4]-Fused 3-Alkenyl-Oxindoles via Propargyl Alcohol-Triggered C(sp³)–H Functionalization

ACS Catalysis, Journal Year: 2021, Volume and Issue: 12(2), P. 943 - 952

Published: Dec. 30, 2021

[3,4]-Fused oxindoles are the core structures of naturally occurring oxindole alkaloids, and fused tricyclic have distinguished themselves with unique biological activities. Herein, we developed a synthetic strategy for divergent synthesis diverse types [3,4]-seven- or six-membered ring-fused 3-alkenyl-oxindoles incorporating benzazepine significant building blocks from propargyl alcohols via cascade nucleophilic substitution/site-selective hydride transfer/cyclization process unprecedentedly. In addition, variety nucleophiles, including H2O, were available controllable construction wide range conjugated alkenes, ketones, allyl encompassing natural products pharmaceutical motifs utilization 4-amine substituted isatins widespread terminal alkyne-derived alcohols. Furthermore, utility methodology mechanistic studies also well presented.

Language: Английский

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Recent Advances in Mono‐ and Difunctionalization of Unactivated Olefins

Asian Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 10(12), P. 3201 - 3232

Published: Nov. 5, 2021

Abstract Olefins are synthetically useful building blocks in modern organic synthesis. Direct functionalization of olefins; represent one the most explored transformations synthetic chemistry due to their easy availability and reactivity towards large number reactants affording diverse range compounds. In recent times, development new protocols for olefins is a growing realm. A plethora olefin methodologies have been reported literature through ionic free radical mechanisms including single electron transfer (SET) last two decades. This review gives an overview mono‐ difunctionalization unactivated olefins, with emphasis on mechanistic details.

Language: Английский

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Recent Advances in 1,2‐Amino(hetero)arylation of Alkenes

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(12)

Published: April 23, 2022

Alkene amino(hetero)arylation presents a highly efficient and straightforward strategy for direct installation of amino groups heteroaryl rings across double bond simultaneously. An extensive array practical transformations has been developed via alkene difunctionalization approach to access broad range medicinally valuable (hetero)arylethylamine motifs. This review recent progress in 1,2-amino(hetero)arylation alkenes organized three different modes. First, intramolecular employing C, N-tethered will be introduced. Next, two-component reactions discussed with combination precursors, external aryl precursor, C-tethered amine or reagents, alkenes. Last, three-component intermolecular covered.

Language: Английский

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A Counterion/Ligand-Tuned Chemo- and Enantioselective Copper-Catalyzed Intermolecular Radical 1,2-Carboamination of Alkenes

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(39), P. 18081 - 18089

Published: Sept. 26, 2022

The copper-catalyzed enantioselective intermolecular radical 1,2-carboamination of alkenes with readily accessible alkyl halides is an appealing strategy for producing chiral amine scaffolds. challenge arises from the easily occurring atom transfer addition between and issue enantiocontrol. We herein describe a alkene sulfoximines in highly chemo- manner. key to success this process conceptual design counterion/highly sterically demanded ligand coeffect promote exchange copper(I) forge C–N bonds radicals copper(II) complex. reaction covers bearing distinct electronic properties, such as aryl-, heteroaryl-, carbonyl-, aminocarbonyl-substituted ones, various precursors, including chlorides, bromides, iodides, CF3 source. Facile transformations deliver many building blocks interest organic synthesis related areas.

Language: Английский

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Recent advances in the synthesis of 2,3-fused quinazolinones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(32), P. 6293 - 6313

Published: Jan. 1, 2022

As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.

Language: Английский

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Organic photoredox catalytic radical sulfonamidation/cyclization of unactivated alkenes towards polycyclic quinazolinones

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6290 - 6294

Published: Jan. 1, 2022

The synthesis of sulfonamidylated polycyclic quinazolinones was developed via visible-light-induced radical sulfonamidation/cyclization unactivated alkenes using 4CzIPN as the photocatalyst.

Language: Английский

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Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

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Modular and Practical 1,2‐Aryl(Alkenyl) Heteroatom Functionalization of Alkenes through Iron/Photoredox Dual Catalysis**

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(44)

Published: Sept. 13, 2023

Abstract Efficient methods for synthesizing 1,2‐aryl(alkenyl) heteroatomic cores, encompassing heteroatoms such as nitrogen, oxygen, sulfur, and halogens, are of significant importance in medicinal chemistry pharmaceutical research. In this study, we present a mild, versatile practical photoredox/iron dual catalytic system that enables access to highly privileged pharmacophores with exceptional efficiency site selectivity. Our approach exhibits an extensive scope, allowing the direct utilization wide range commodity or commercially available (hetero)arenes well activated unactivated alkenes diverse functional groups, drug scaffolds, natural product motifs substrates. By merging iron catalysis photoredox cycle, vast array alkene functionalization products incorporate neighboring azido, amino, halo, thiocyano nitrooxy group were secured. The scalability ability rapid synthesize numerous bioactive small molecules from readily starting materials highlight utility protocol.

Language: Английский

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Nitrative Difunctionalization of Alkenes via Cobalt-Mediated Radical Ligand Transfer and Radical-Polar Crossover Photoredox Catalysis

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(24), P. 16136 - 16147

Published: Dec. 1, 2023

Herein, we report the rational design of a modular dual photoredox and cobalt catalysis paradigm for difunctionalization unsaturated hydrocarbons, unlocking synthesis valuable but challenging 1,2-halonitroalkane substrate class. The protocol relies on use redox-active organic nitrating reagent N-nitrosuccinimide as source nitryl radicals cobalt-mediated radical ligand transfer (RLT) methodology to form carbon–halogen bond. This synergistic cooperation between photocatalyst high-valence metal center occurs under mild reaction conditions is capable delivering 1,2-chloronitro- 1,2-bromonitroalkanes in single chemical operation while exhibiting high functional-group tolerance exclusive regioselectivity variety olefins. Mechanistic studies based both experimental spectroscopic analysis provided insights into nature this catalytic halo-nitration process including evidence halogen catalyst. Furthermore, employing net-neutral radical/polar crossover (RPC) approach cobalt-free allowed us accommodate external protic nucleophiles, thiols, alcohols, acids, and, notably, substituted amines. Highly functionalized olefin scaffolds also successfully underwent nitrative difunctionalization, demonstrating viability these protocols late-stage functionalization bioactive molecules.

Language: Английский

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