Photosensitized Imino-Thiocyanation of Alkenes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 17, 2025

A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent S-cyano-N-(diphenylmethylene) thiohydroxylamine. wide range were successfully transformed into corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its nature, broad substrate compatibility, and atom step economy, providing an effective strategy assembling β-amino thiocyanate-containing scaffolds.

Язык: Английский

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Energy‐Transfer Enabled 1,4‐Aryl Migration

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 5, 2024

Abstract Functional group translocation is undoubtedly a pivotal synthetic transformation in organic chemistry. Numerous types of reactions involving radical 1,2‐aryl or 1,4‐aryl migration via electron transfer mechanism have been extensively investigated. Nevertheless, energy‐transfer enabled 1,4‐arylation remains unknown. Herein we disclose that an unprecedented di‐π‐ethane rearrangement featuring facilitated by energy catalysis under visible light conditions. The newly developed mild protocol exhibits tolerance towards diverse functional groups and enables the multitude aromatic rings, encompassing both electron‐withdrawing electron‐rich groups. open‐shell strategy has also found successful application modification several drugs. Large‐scale experiments, continuous‐flow experiment, versatile manipulation products demonstrated robustness potential utility this method. Preliminary mechanistic studies supported involvement species provided evidence for mechanism.

Язык: Английский

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Norrish-Yang-type cyclopropanation via functional group migration with photosensitizer at ppb loading

Chem Catalysis, Год журнала: 2024, Номер unknown, С. 101099 - 101099

Опубликована: Сен. 1, 2024

Язык: Английский

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Photoinduced Pd-Catalyzed Formal Asymmetric Allylic Substitution of Piperidine Scaffolds

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4384 - 4393

Опубликована: Фев. 26, 2025

Язык: Английский

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Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration

Tetrahedron Letters, Год журнала: 2025, Номер 159, С. 155516 - 155516

Опубликована: Фев. 27, 2025

Язык: Английский

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Blue Light-Induced Diazo Cross-Coupling: Synthesis of Allyldiazo Compounds through Reshuffling of Functionalities

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

In this paper, we describe a new type of cross-coupling between simple diazo and vinyldiazo compounds that gives access to unusual allyldiazo products. Blue light discriminates two towards free carbene formation, triggering sequential cyclopropenation, (3+2) cycloaddition ring opening rearrangement processes. This strategy involves an overall reshuffle functionality olefinic carbons with extrusion nitrogen. Mechanistic studies including 15N-labelling experiment demonstrate the products derives from compounds, while reagents are selectively decomposed via energy transfer thioxanthone photocatalyst. The obtained can be efficiently converted into synthetically useful structures such as 1,3-dienes, gem-difluoro-1,4-diene, hydrazine, dihydropyrazole, pyridazine, bicyclobutane.

Язык: Английский

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Highly Diastereoselective Synthesis of 5/6-Fused Bicyclic Ring Systems via Radical Cyano Group Migration

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 3, 2025

Here we report a highly diastereoselective cyano group transfer radical cyclization reaction to construct 5/6-fused bicyclic ring systems that bear three contiguous and congested stereogenic elements, with 100% atom economy under catalyst-free near-ultraviolet light irradiation conditions. Mechanistic investigations density functional theory calculations suggest the diastereoselectivity is governed by conformational distribution of triplet diradical intermediate rate reverse intersystem crossing (RISC) before coupling.

Язык: Английский

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In Situ Synthesis of MIL-101 on Carboxyl-Functionalized SBA-16: Preparation and Catalytic Performance in the Knoevenagel Condensation Reaction under Mild Conditions

Journal of environmental chemical engineering, Год журнала: 2025, Номер unknown, С. 116267 - 116267

Опубликована: Март 1, 2025

Язык: Английский

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Oxa-π, σ-Methane Rearrangement Approach for Epoxide Synthesis

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Март 30, 2025

Epoxides are significant chemicals that utilized across various fields. Here, we describe an unprecedented photochemical rearrangement approach for synthesizing a diverse collection of epoxides enabled by energy transfer catalysis under visible light conditions. The process enables the easy preparation α-amino-substituted epoxide derivatives with broad substrate scope, functional group tolerance, and mild reaction Furthermore, this photorearrangement has also been applied in complex architectures, could be easily transferred to amino alcohol derivatives. Overall, oxa-π, σ-methane provides complementary strategy existing methods through catalysis.

Язык: Английский

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Visible Light-Mediated Aza-Norrish–Yang Type Cyclization

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6473 - 6485

Опубликована: Апрель 6, 2025

Язык: Английский

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