α-Haloenamides: Synthesis and Subsequent Transformations

Synthesis, Год журнала: 2022, Номер 55(01), С. 27 - 44

Опубликована: Авг. 9, 2022

Abstract The aim of this Short Review is to give an updated overview the synthesis α-haloenamides, which constitute a versatile subclass enamides. α-Haloenamides can be prepared from ynamides, acetamides, or gem-dibromoalkenes in presence N-nucleophiles and easily converted into more elaborated structures through halogen-metal exchange transition-metal-catalyzed cross-coupling reactions. 1 Introduction 2 α-Haloenamide Synthesis 2.1 Hydrohalogenation Ynamides 2.1.1 cis-Hydrohalogenation 2.1.2 trans-Hydrohalogenation 2.2 α,β-Dihalogenation 2.2.1 lodochlorination Iodobromination 2.2.2 Iodofluorination 2.3 Chloroselenation 2.4 Carbohalogenation 2.4.1 Carboiodination 2.4.2 Chloroallylation 2.4.3 Chloro-benzhydrylation 2.4.4 Chloro-γ-hydroxylation 2.5 Vilsmeier–Haack Reactions 2.6 Cross-Coupling Reaction gem-Dibromoalkenes Presence N-Nucleophiles 3 Transformations 3.1 Suzuki Sonogashira 3.2 Heck 3.3 Stille 3.4 Miscellaneous Applications Carbonylation 3.4.2 Reduction 3.4.3 α-Fluoroimides 3.4.4 Palladium-Catalyzed Intramolecular Cyclization 4 Conclusion

Язык: Английский

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Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide

Synthesis, Год журнала: 2021, Номер 53(16), С. 2889 - 2896

Опубликована: Апрель 21, 2021

Abstract A rare-earth salt Yb(OTf)3-catalyzed regioselective hydroamination of ynamides with anilines and p-toluenesulfonamide has been developed. This protocol provided facile access to a diverse range amidines good functional group tolerance in moderate high yields.

Язык: Английский

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An alternative approach to selenides and diselenides from Se(0) and epoxides/aziridines under sustainable conditions

ARKIVOC, Год журнала: 2023, Номер 2023(5)

Опубликована: Фев. 18, 2023

The on-water reduction of elemental selenium promoted by rongalite (sodium hydroxymethanesulfinate)/sodium hydroxide provided selenide anions, which led to a variety β-hydroxy and βamino selenides upon reaction with epoxides aziridines through an alternative sustainable approach.The reactions are operationally simple occur in highly regioselective enantioconservative way.The preparation diselenides was also accomplished different approach relies on the generation diselenide dianions from sodium borohydride.Reaction three-membered heterocycles differently substituted β-amino diselenides.

Язык: Английский

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An I₂O₅/KSCN-Mediated Iodothiocyanation of Alkynes

Acta Chimica Sinica, Год журнала: 2024, Номер 82(1), С. 5 - 5

Опубликована: Янв. 1, 2024

Thiocyanates are an important compound family that widely found in natural products and active pharmaceutical ingredients.In addition, their ability to function as versatile electrophiles either on sulfur or carbon centers enables them especially valuable intermediates synthetic organic chemistry.In the past decades, considerable advances for synthesis of thiocyanates have been made.However, most rely transition-metal promotion suffer from harsh reaction conditions limited substrate scope.Therefore, efficient practical accesses highly desirable.Herein, we disclose herein a general access (E)-β-iodo vinylthiocyanates via iodothiocyanation alkynes with I2O5 KSCN.In contrast previous methods, present strategy holds advantages free, high diasteroselectivity, scaled-up grams mild conditions.By treatment KSCN at room temperature, wide variety terminal and/or internal all gave corresponding yields excellent chemoselectivities.In desired were also obtained good both aryl simple alkyl substituted alkynes.Interestingly, propargyl alcohol was effective substrate.Furthermore, several propionates afforded mixture regio-isomers.Treatment herbicide clodinafop-propargyl resulted yield vinylthiocyanates, which indicated this could be applied direct modification drugs.Finally, can smoothly gram level, indicates it industrial pharmaceuticals.

Язык: Английский

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Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(16), С. 11272 - 11280

Опубликована: Авг. 1, 2024

Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent access 4-(selanyl)isoquinoline-

Язык: Английский

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