Visible-Light-Induced Regioselective Radical-Polar Crossover 1,4-Hydrophosphinylation of 1,3-Enynes: Access to Trisubstituted Allenes Bearing a Phosphine Oxide Group

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4678 - 4683

Опубликована: Май 24, 2024

The radical 1,4-functionalizations of 1,3-enynes have emerged as a powerful strategy for the synthesis multisubstituted allenes. However, phosphorus-centered radical-initiated transformations remain largely elusive. Herein, visible-light photoredox catalytic regioselective hydrophosphinylation with diaryl phosphine oxides phosphinoyl precursors has been realized. This protocol features mild conditions, wide substrate scope, and good functional group tolerance, producing diverse range phosphinoyl-substituted allenes in moderate to yields high atom economy. Detailed mechanistic experiments revealed radical-polar crossover process reaction.

Язык: Английский

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Electrochemically mediated synthesis of trifluoromethylallenes

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3485 - 3490

Опубликована: Янв. 1, 2024

Herein, we report electrochemically mediated trifluoromethylallene synthesis via the rearrangement of trifluoromethyl-containing 1,3-enynes under action silicon or boron radicals, with good selectivity and without external oxidants.

Язык: Английский

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Visible-light-induced decarboxylative annulation of silanecarboxylic acids with 2‑isocyanobiaryls to 6‑silyl-substituted phenanthridines

Molecular Catalysis, Год журнала: 2024, Номер 560, С. 114098 - 114098

Опубликована: Апрель 12, 2024

Язык: Английский

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Visible light promoted synthesis of allenes

Catalysis Science & Technology, Год журнала: 2024, Номер 14(18), С. 5143 - 5160

Опубликована: Янв. 1, 2024

This review article summarizes the visible light mediated synthesis of allenes from substrates like 1,3-enynes, propargylic carbonates, homopropargylic alcohols, oxalates, alkynyl diazo compounds, and terminal aziridines.

Язык: Английский

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Enantio- and Regioselective Ni-Catalyzed Radical Relay 1,4-Arylalkylation of 1,3-Enynes to Access Chiral Tetrasubstituted Allenes

ACS Catalysis, Год журнала: 2024, Номер 14(18), С. 13940 - 13946

Опубликована: Сен. 5, 2024

Язык: Английский

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Regioselectivity of conjugate addition of secondary amines and thiols to α-substituted enyne aldehydes

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134494 - 134494

Опубликована: Янв. 1, 2025

Язык: Английский

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Photocatalyzed Deuterodichloromethylation of Olefins Using Silacarboxylic Acids as Halogen‐Atom Transfer Reagents

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

Опубликована: Март 7, 2025

Abstract A visible‐light‐induced deuterodichloromethylation of alkenes was developed with readily available and inexpensive deuterochloroform as the reagent. Silacarboxylic acids, which could generate silyl radicals through efficient decarboxylation, were applied halogen atom transfer agents. series deuterium‐containing gem ‐dichloroalkanes prepared in good yields.

Язык: Английский

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Transition‐Metal‐Free Visible‐Light‐Induced Alkynylation of Silacarboxylic Acids

ChemistrySelect, Год журнала: 2025, Номер 10(15)

Опубликована: Апрель 1, 2025

Abstract An operationally simple and mild protocol for the visible‐light‐induced intermolecular coupling of silacarboxylic acids with sulfonyl alkynes to form alkynylsilanes is presented. This study highlights use inexpensive readily available 4CzIPN as a photocatalyst, along more stable silyl radical precursors, enabling synthesis variety in good excellent yields, notably without need transition metals. The transformation offers several key advantages, including broad substrate scope, functional group tolerance, compatibility heterocyclic substrates. Furthermore, both scale‐up reaction late‐stage functionalization natural products have been successfully achieved under conditions. These features make process not only efficient but also versatile suitable wide range applications chemical modification.

Язык: Английский

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Photocatalyzed dehalogenative deuteration with silacarboxylic acids as halogen-atom transfer agents

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(17), С. 4757 - 4761

Опубликована: Янв. 1, 2024

A visible light-induced organophotocatalytic strategy for dehalogenative deuteration of a wide variety primary, secondary, and tertiary alkyl bromides is reported.

Язык: Английский

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Nickel-catalyzed regiodivergent sulfonylarylation of 1,3-enynes to access allenes and dienes

Chemical Science, Год журнала: 2024, Номер 15(33), С. 13271 - 13278

Опубликована: Янв. 1, 2024

The radical-mediated difunctionalization of 1,3-enynes facilitates rapid access to structurally diverse allenes and dienes.

Язык: Английский

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