Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

Chemical Reviews, Journal Year: 2021, Volume and Issue: 121(10), P. 5741 - 5829

Published: April 9, 2021

Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance aryl spanning most disciplines chemical sciences, we review recent development chemistry over past seven years (2013-2020). Special emphasis is put on various new transformations involving generation radical intermediates via thermal, photochemical, and electrochemical means. Recent advances transition metal-catalyzed reactions using also reviewed. Together, these newly developed significantly expand synthetic chemist's repertoire aromatic carbon-carbon carbon-heteroatom bond forming methods precursors, providing powerful tools for synthesis modification complex molecular scaffolds.

Language: Английский

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Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(6), P. 2313 - 2382

Published: Jan. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Language: Английский

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Recent Advances in the Construction of Spiro Compounds via Radical Dearomatization

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(21), P. 4446 - 4461

Published: July 15, 2020

Abstract The field in dearomatization of aromatic compounds for the construction spirocycle has been developed rapidly over last two decades and it provides alternative synthetic method without using extra stoichiometric amounts chemical oxidants or reductants. In addition, radical cascade reactions alkenes alkynes that produce multiple bonds one‐step are significant direct efficient building complex molecules. By combining these concepts, opens a new powerful avenue accessing These have well explored past decade. As result, we summarize recent eventful advances this growing area as review, which typical examples listed mechanism also discussed. magnified image

Language: Английский

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Recent Advances in the Catalytic Synthesis of Arylsulfonyl Compounds

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(7), P. 4169 - 4204

Published: March 19, 2021

Arylsulfonyl compounds are among the most important in pharmaceutical and medicinal chemistry. Hence, a wide variety of sulfonylation methods have been reported recently. This review summarizes arylsulfonylation methodologies developed last 5 years includes two major categories. The first entails direct second multicomponent arylsulfonylation. In arylsulfonylation, arylsulfonyl reagents react with C–H activated compounds, alkynes, alkenes through coupling or addition reactions. reactions, arylation various substrates sulfur dioxide surrogates, such as DABSO, Na2S2O5, K2S2O5. hydrazides, aryl boronic acids, silanes, halides widely employed that surrogates to generate an source, ensuing reactions proceed via pathways analogous those

Language: Английский

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Access to axially chiral styrenes via a photoinduced asymmetric radical reaction involving a sulfur dioxide insertion

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(1), P. 164 - 177

Published: Jan. 1, 2022

Language: Английский

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Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: Nov. 18, 2022

Abstract From the viewpoint of synthetic accessibility and functional group compatibility, photoredox-catalyzed sulfur dioxide insertion strategy enables in situ generation functionalized sulfonyl radicals from easily accessible starting materials under mild conditions, thereby conferring broader application potential. Here we present two complementary photoinduced systems to trigger radical asymmetric Truce–Smiles rearrangements for preparing a variety chiral sulfones that bear quaternary carbon stereocenter. This protocol features broad substrate scope excellent stereospecificity. Aside scalability, introduction stereocenter at position β bioactive molecule-derived further demonstrates practicality potential this methodology.

Language: Английский

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The same oxygenation-state introduction of hypervalent sulfur under transition-metal-free conditions

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(23), P. 3956 - 3966

Published: Jan. 1, 2020

This review discusses the application of same oxygenation-state introduction hypervalent sulfur strategy under transition-metal-free conditions.

Language: Английский

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Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

ChemistrySelect, Journal Year: 2020, Volume and Issue: 5(42), P. 13103 - 13134

Published: Nov. 13, 2020

Abstract Sodium sulfinates, sulfinic acids, sulfonyl chlorides and hydrazides as readily available efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these via different methods, then the could react with various substrates pathways to afford corresponding products. In this review, we will summarize progress reaction using sodium three terms of reagents, classify reactions into four types: 1. Sulfonylation sulfinates. 2. acid. 3. chlorides. 4. hydrazides.

Language: Английский

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The Same Oxidation‐State Introduction of Hypervalent Sulfur via Transition‐Metal Catalysis

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(12), P. 3338 - 3355

Published: Jan. 26, 2021

Abstract Sulfonyl compounds have attracted considerable interest due to their extensive applications in drug discovery, agricultural, and material science. The access the assembly of SO 2 ‐containing via same oxidative‐state introduction hypervalent sulfur has come fore recent years. Especially, transition‐metal‐involved synthesis is most effective strategy since easy insert into metal‐carbon bonds. This review discusses application oxidation‐state under transition‐metal‐catalyzed conditions, presents according different metal catalysts synthesized diversity sulfur‐containing skeletons, including sulfonamides, sulfones, sulfinamides, sulfonyl acids fluorides.

Language: Английский

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Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts

Organic Letters, Journal Year: 2022, Volume and Issue: 24(15), P. 2955 - 2960

Published: April 13, 2022

A photoredox-catalyzed sulfonylation of silyl enol ethers with DABCO·(SO2)2 and thianthrenium salts is achieved, providing diverse β-keto sulfones in moderate to good yields. This protocol features easily accessible starting materials functional group compatibility, enabling the introduction various functionalized sulfonyl groups into ketones. Furthermore, as one important industrial raw materials, methanol can be employed methyl source prepare α-methylsulfonated ketones through a intermediate for first time.

Language: Английский

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