“In-Water” Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(35), С. 13336 - 13351

Опубликована: Авг. 22, 2024

An environmentally friendly multicomponent reaction strategy for the synthesis of functionally rich all-carbon substituted 2,3-dihydro-1H-pyrrol-2-ols "in-water" at room temperature has been reported. Water plays an indispensable role in presence readily available catalytic surfactants sodium dioctylsulfosuccinate and dodecyl sulfate to effectuate transformation, as proved by inferior results obtained organic solvents. A wide display substrate scope functional group compatibility permits diversity generation a mild operationally simple fashion. High product yields, fast rate, recoverability/recyclability catalysts, high TON/TOF, ease purification final products filtration, AE values, excellent E-factor count with score low possible highlight "greenness" this approach. Feasibility "gram-scale" synthetic elaboration offer notable advantages. The mechanistic understanding intercepting labile "imine" intermediate realized through sequence imine formation Mannich-type followed intramolecular N-cyclization.

Язык: Английский

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Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C–N Coupling

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

Modular C–N coupling is a desirable way to construct N-aryl carbamates, which are privileged scaffolds in active pharmaceutical ingredients. However, there no broadly applicable metal-free methods for theN-arylation of carbamates. Herein, we describe approach that uses aryl(TMP)iodonium salts as arylation reagents cyclic carbamates by exploiting the metal-like reactivity iodine(III). The scope includes 25 examples, including 17 different and 9 yields ranging between 55 97% (75% avg).

Язык: Английский

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CuF₂/DTBP-Catalyzed Chan-Lam Coupling of Oxazolidinones with Arylboronic Acid Pinacol Ester: Scope and Application

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 25, 2025

A new combination of CuF2/DTBP-catalyzed N-arylation oxazolidinones, amides, amines, and azoles has been explored with arylboronic acid pinacol esters (arylBpin). This methodology also applied to the synthesis oxazolidinone-based marketed drugs, including Rivaroxaban, Linezolid, Sutezolid, Toloxatone. Mechanistic investigations using various spectroscopic techniques DFT studies revealed role DTBP/MeOH in catalytic process.

Язык: Английский

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Metal-free iodosulfonylation of alkynes to access (E)-β-iodovinyl sulfones in water

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

We report a metal-free iodosulfonylation of alkynes in water at room temperature, which efficiently produces ( E )-β-iodovinyl sulfones good to excellent yields with high regio- and stereoselectivity.

Язык: Английский

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