Hypervalent Iodine-Mediated Azidation Reactions

Hypervalent Iodine-Mediated Azidation Reactions

Detalhes bibliográficos
Parent link:	European Journal of Organic Chemistry Vol. 2022, iss. 34.— 2022.— [e202200754, 24 p.]
Autor Corporativo:	Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий (ИШХБМТ)
Outros Autores:	Mironova I. A. Irina Andreevna, Kirsch S. F., Zhdankin V. V. Viktor Vladimirovich, Yoshimura A. Akira, Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich)
Resumo:	Title screen Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one-step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generated in situ from common hypervalent iodine reagents (such as diacetoxyiodobenzene or iodosylbenzene) and a source of azide anion (TMSN3 or NaN3). The second part of review is dedicated to the application of stable azidobenziodoxoles as useful azidating reagents that allow selective direct azidation of C?H bonds or double carbon-carbon bonds under mild reaction conditions. The use of azidobenziodoxoles eliminates the main disadvantages of the traditional approaches to organic azides, such as the need in pre-functionalization of organic substrates and harsh reaction conditions. Synthetic application of azidobenziodoxoles made possible direct selective azidation of a plethora of organic substrates including complex molecules at the late synthetic stage.
Idioma:	inglês
Publicado em:	2022
Assuntos:	электронный ресурс труды учёных ТПУ azide azidation hypervalent compounds hypervalent iodine iodine азиды гипервалентные соединения гипервалентный йод
Acesso em linha:	https://doi.org/10.1002/ejoc.202200754
Formato:	Recurso Electrónico Capítulo de Livro
KOHA link:	https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=668675

Registos relacionados

Hypervalent iodine in the structure of N-heterocycles: synthesis, structure, and application in organic synthesis
Publicado em: (2020)

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle
Publicado em: (2018)

Zefirov's reagent and related hypervalent iodine triflates
Por: Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich)
Publicado em: (2021)

Synthesis of 2-fluorobenzoic acids by nucleophilic fluorination of 1-arylbenziodoxolones
Publicado em: (2022)

Preparation and X-ray structure of 2-iodoxybenzenesulfonicacid (IBS) – a powerful hypervalent iodine(V) oxidant
Publicado em: (2018)

Application of hypervalent iodine compounds in advanced green technologies
Por: Zhdankin V. V.
Publicado em: (2021)

Synthesis of Oxazoline and Oxazole Derivatives by Hypervalent-Iodine-Mediated Oxidative Cycloaddition Reactions
Publicado em: (2020)

Imino‐λ3‐iodane and Catalytic Amount of I2‐Mediated Synthesis of N‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement
Publicado em: (2020)

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines
Publicado em: (2021)

Benziodoxole-Derived Organosulfonates: The Strongest Hypervalent Iodine Electrophiles and Oxidants
Publicado em: (2020)

Preparation, Structure, and Reactivity of Pseudocyclic β-Trifluorosulfonyloxy Vinylbenziodoxolone Derivatives
Publicado em: (2021)

Iodonium Salts as Benzyne Precursors
Por: Yoshimura A. Akira
Publicado em: (2018)

Iodonium ylides in organic synthesis
Por: Yusubov M. S. Mekhman Suleiman-Ogly (Suleimanovich)
Publicado em: (2016)

Preparation, X-ray Structure, and Reactivity of Triisopropylsilyl-Substituted Aryliodonium Salts
Publicado em: (2015)

Efficient Catalytic Synthesis of Condensed Isoxazole Derivatives via Intramolecular Oxidative Cycloaddition of Aldoximes
Publicado em: (2022)

Thermal stability of N-heterocycle-stabilized iodanes – a systematic investigation
Publicado em: (2019)

Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications
Publicado em: (2023)

Generation of benzyne from aryl benziodoxaborole triflate under aqueous conditions and its reactions with alkyl aryl sulfides
Publicado em: (2024)

Intramolecular amination via acid-catalyzed rearrangement of azides: a potent alternative to intermolecular direct electrophilic route
Por: Stankevich K. S. Kseniya Sergeevna
Publicado em: (2021)

Site Selective Concerted Nucleophilic Aromatic Substitutions of Azole-Ligated Diaryliodonium Salts
Publicado em: (2023)

Halogen Bonding Provides Heterooctameric Supramolecular Aggregation of Diaryliodonium Thiocyanate
Publicado em: (2020)

Azidation of Partially Protected Carbohydrate Derivatives: Efficient Suppression of Acyl Migration
Publicado em: (2020)

The chemistry of heterocycles in the 21st century
Publicado em: (2024)

A New, Simple, and General Synthesis of N-Oxides of Iodopyridines and Iodoquinolines via the Diazotization–Iodination of Heterocyclic Amino N-Oxides in the Presence of p-Toluenesulfonic Acid in Water
Por: Krasnokutskaya E. A . Elena Aleksandrovna
Publicado em: (2018)

Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents
Publicado em: (2018)

Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
Publicado em: (2018)

Effect of electric field on the explosive sensitivity of silver azide
Publicado em: (2016)

m-Iodosylbenzoic acid, a tagged hypervalent iodine reagent for the iodo-functionalization of alkenes and alkynes
Publicado em: (2008)

The Effect of Additionally Introduced Impurities of Fe and Pb Ions on Silver Azide Decomposition
Publicado em: (2017)

The Effect of Magnetic Field on Crystallization and some Properties of Silver Azide Crystals
Publicado em: (2018)

Influence of the thickness of flat crystals on the critical temperature of thermal explosion of lead azide
Por: Khaneft A. V. Aleksandr Villivich
Publicado em: (2016)

2-Iodoxybenzoic acid ditriflate: the most powerful hypervalent iodine(v) oxidant
Publicado em: (2019)

Cyclotron Production of Iodine-124
Por: Salodkin S. S. Stepan Sergeevich
Publicado em: (2020)

Hypervalent iodine compounds: synthesis, structure and its applications in aqueous media
Publicado em: (2020)

Size effect of lead azid initiation by CO[2] laser radiation
Publicado em: (2016)

Investigation of preparative possibilities of iodinating systems on the basis of N-iodoacetamide
Publicado em: (2007)

Preparation and X-ray Structures of 3-[Bis(trifluoroacetoxy)iodo]benzoic Acid and 3-[Hydroxy(tosyloxy)iodo]benzoic Acid: New Recyclable Hypervalent Iodine Reagents
Publicado em: (2008)

Potassium 4-Iodylbenzenesulfonate (PIBS) as a convenient water-soluble reagent based on hypervalent iodine
Por: Mironova I. A. Irina Andreevna
Publicado em: (2015)

DFT investigation of the thermodynamics and mechanism of electrophilic chlorination and iodination of arenes
Publicado em: (2011)

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid
Publicado em: (2018)