Chemical Reviews, Год журнала: 2024, Номер unknown
Опубликована: Сен. 13, 2024
Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.
Язык: Английский
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34Stereoselective synthesis of substituted 1,3-dienes from propargylic esters: electrophilic-metal or redox catalysis?
Science China Chemistry, Год журнала: 2024, Номер 67(5), С. 1384 - 1396
Опубликована: Март 22, 2024
Язык: Английский
Процитировано
10Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Июнь 28, 2024
1,2-Difunctionalization of alkynes offers a straightforward approach to access polysubstituted alkenes. However, simultaneous multi-component cascade transformations including difunctionalization two with both syn- and anti-selectivity in one catalyst system is undeveloped proves be significant challenge. Herein, we report Nickel-catalyzed four-component reaction 1,3-dienes using terminal alkynes, aryl boroxines, perfluoroalkyl iodides, wherein the forms three new C-C bonds single vessel serve as modular strategy excellent chemoselectivity, good regioselectivity exclusive stereoselectivity. Control experiments reveal plausible mechanism DFT calculations explain cause for formation this unusual reaction. Furthermore, successfully incorporate biologically active units into 1,2,3,4-tetrasubstituted 1,3-dienes, which greatly increases diversity molecular scaffolds brings more potential values medicinal chemistry, synthetic utility our protocol further demonstrated by late-stage transformations.
Язык: Английский
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9Integrating Olefin Carboamination and Hofmann‐Löffler‐Freytag Reaction by Radical Deconstruction of Hydrazonyl N−N Bond
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(17)
Опубликована: Фев. 21, 2024
As a type of elementary organic compounds containing N-N single bond, hydrazone involved chemical conversions are extremely extensive, but they mainly limited to N
Язык: Английский
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6Stereoselective Synthesis of Polysubstituted Conjugated Dienes Enabled by Photo‐Driven Sequential Sigmatropic Rearrangement
Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(24)
Опубликована: Апрель 8, 2024
We here reported a highly stereoselective method for the synthesis of polysubstituted conjugated dienes from α-aryl α-diazo alkynyl ketones and pyrazole-substituted unsymmetric aminals under mild conditions, which was promoted by photo-irridation involved with 1,6-dipolar intermediate quadruple sigmatropic rearrangements, successfully developed. In this transformation, cleavage four bonds recombination five were implemented in one operational step. This protocol provided modular tool constructing amines, pyrazoles α-alkynyl-α-diazoketones one-pot manner. The results mechanistic investigation indicated that plausible reaction path underwent 1,6-sigmatropic rearrangement instead 1,5-sigmatropic rearrangement.
Язык: Английский
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6Synthesis of highly substituted 1,3-dienes through halonium promoted 1,2-sulfur migration of propargylic thioethers
Chemical Communications, Год журнала: 2024, Номер 60(13), С. 1794 - 1797
Опубликована: Янв. 1, 2024
Highly regio- and diastereoselective synthesis of 2-thiorganyl 1-bromo or 1-iodo-1,3-dienes is reported via 1,2-sulfur migration propargylic sulfides. These dienes are precursors thiophenes selenophenes by reaction with sulfur selenium.
Язык: Английский
Процитировано
4Anion Relay Chemistry Enables Stereoselective Carbonyl-Alkyne Metathesis Reactions
Organic Letters, Год журнала: 2024, Номер 26(36), С. 7601 - 7606
Опубликована: Сен. 4, 2024
Dithiane chemistry is increasingly advantageous in the development of novel anion relay (ARC) modes that harness their umpolung properties to address new chemical challenges. Herein, we report use an ARC strategy promote regioselective carbonyl alkyne metathesis (CAM) various compounds with alkynyl 1,3-dithianes. Notably, this transformation provides a platform for obtaining stereodefined polysubstituted 1,3-dienes.
Язык: Английский
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4Palladium-Catalyzed Intermolecular 1,3-Dienylation of Propargyl Esters Involving the Insertion of SO2
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 20, 2025
A palladium-catalyzed three-component 1,3-dienylation of propargylic esters with DABSO and aryl iodides has been developed. This novel reductive cross-coupling reaction produces 2-sufonylated 1,3-dienes as single products in the presence metal Mn high regio- chemoselectivities. Control experiments demonstrated that transformation may undergo a radical process.
Язык: Английский
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0Recent advances in controllable/divergent synthesis
Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 890 - 914
Опубликована: Май 7, 2025
The development of streamlined methodologies for the expeditious assembly structurally diverse organic architectures represents a paramount objective in contemporary synthetic chemistry, with far-reaching implications across pharmaceutical development, advanced materials innovation, and fundamental molecular science research. In recent years, controllable/divergent strategies functional molecules using common starting have garnered significant attention due to their high efficiency. This review categorizes literatures focusing on key regulatory factors product divergent formation, which controlling chemical selectivity primarily relies ligands, metal catalysts, solvents, time, temperature, acids/bases, subtle modifications substrates. To gain deeper understanding mechanisms underlying reaction activity differentiation, provides systematic analysis critical steps through specific case studies. It is hoped that synthesis concept will spark interest practitioners aficionados delve into discipline pursue novel advancements realm synthesis.
Язык: Английский
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0Copper-Catalyzed Dienylation of Aldehydes Using Propargylic Carbonates
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 20, 2025
A copper-catalyzed dienylation of aldehydes using propargylic carbonates in the presence B2pin2 has been successfully developed, enabling synthesis a diverse range substituted 1,3-butadienyl-2-carbinols (BDCs). This innovative approach circumvents requirement allene reagents and provides an alternative protocol that allows access to BDCs. In addition, synthetic value products demonstrated series further conversions, reaction mechanism proposed based on control experiments.
Язык: Английский
Процитировано
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