Visible-Light-Driven Bifunctional Photocatalytic Radical-Cascade Selenocyanation/Cyclization of Acrylamides with KSeCN

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5783 - 5796

Опубликована: Апрель 9, 2024

A visible-light-induced radical-cascade selenocyanation/cyclization of N-alkyl-N-methacryloyl benzamides, 2-aryl-N-acryloyl indoles, and N-methacryloyl-2-phenylbenzimidazoles with potassium isoselenocyanate (KSeCN) was developed. The reactions were carried out inexpensive KSeCN as a selenocyanation reagent, persulfate an oxidant, 2,4,6-triphenylpyrylium tetrafluoroborate bifunctional catalyst for phase-transfer catalysis, photocatalysis. library selenocyanate-containing isoquinoline-1,3(2H,4H)-diones, indolo[2,1-a]isoquinoline-6(5H)-ones, benzimidazo[2,1-a]isoquinolin-6(5H)-ones achieved in moderate to excellent yields at room temperature under visible-light ambient conditions. Importantly, the present protocol features mild reaction conditions, large-scale synthesis, simple manipulation, product derivatization, good functional group, heterocycle tolerance.

Язык: Английский

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Photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade

Chemical Communications, Год журнала: 2024, Номер 60(40), С. 5334 - 5337

Опубликована: Янв. 1, 2024

A photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade is developed. The protocol features broad substrate scope and excellent functional group compatibility.

Язык: Английский

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Decarbonylative and Dehydrogenative Cascade Annulation of N‐(o‐Cyanobiaryl)acrylamides with Aldehydes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2835 - 2841

Опубликована: Май 3, 2024

Abstract Decarbonylative and dehydrogenative cascade annulation of aldehydes with N ‐( o ‐cyanobiaryl)acrylamides was developed for the synthesis a broad spectrum alkyl‐ carbonyl‐substituted pyrido[4,3,2‐ gh ]phenanthridines. Secondary tertiary can undergo decarbonylative under DTBP/malonic acid conditions, while aryl, primary, secondary reaction TBHP system. Such transformations were triggered by alkyl acyl radicals, annulations accomplished through intramolecular additions carbon‐centered radical to nitrile group iminyl aromatic ring.

Язык: Английский

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Oxidative cascade cyclization of N-arylacrylamides with TMSN₃

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(6), С. 1186 - 1193

Опубликована: Янв. 1, 2024

An azido-radical-triggered cyclization of

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