Photocatalyst-Free Activation of Sulfamoyl Chlorides for Regioselective Sulfamoyl-Oximation of Alkenes via Hydrogen Atom Transfer (HAT) and Halogen-Atom Transfer (XAT) Relay Strategy

Organic Letters, Год журнала: 2024, Номер 26(10), С. 2062 - 2067

Опубликована: Март 7, 2024

The use of readily available and diverse sulfamoyl chlorides for synthesizing sulfonamide compounds presents an intriguing, yet significantly underexplored strategy. Activating via single-electron reduction poses challenges due to their high potential. Alternatively, the SO2–Cl bond in could be cleaved by XAT. However, existing methodologies have been limited either photocatalyst or monofunctionalization activated alkenes. Here, we report a regioselective sulfamoyl-oximation alkenes involving activation through HAT XAT relay strategy photocatalyst-free way. key this success lies dual roles tert-butyl nitrite (TBN), which not only serves as source oximes but also acts reagent generate crucial reactive species. exclusion metal catalysts photosensitizers utilizing light energy renders protocol versatile universally applicable broad range structurally oxime-containing alkyl sulfonamides.

Язык: Английский

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Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3578 - 3584

Опубликована: Июнь 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Язык: Английский

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Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines

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

Опубликована: Март 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Язык: Английский

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Transition-Metal Free Approaches to Access N-Heterocycles and Valuable Intermediates from Aryldiazonium Salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 13, 2024

Development of novel and efficient synthetic methods to achieve valuable N-heterocycles from aryldiazonium salts has been an important research area in organic chemistry for several decades.

Язык: Английский

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Iron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 18, 2024

A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl undergo halogen atom transfer methyl radicals to form in reactions initiated by a combination

Язык: Английский

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