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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Asymmetric acylarylation of vinylarenes with aldehydes

Trends in Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Photocatalytic Strecker-Type Reaction for the Synthesis of Primary α-Aminonitriles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 17, 2025

A practical photoinduced direct N–O cleavage of oxime ethers via a single electron transfer (SET) process was developed, enabling controlled generation N–H imines iminyl radical intermediates. By employing this strategy, an efficient Strecker-type reaction established to construct variety primary α-aminonitriles using TMSCN as cyanide source. This protocol showed exceptional tolerance various functional groups, delivering the corresponding products in good yields. Mechanistic investigations indicate involvement radicals and radical/polar crossover sequence.

Язык: Английский

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Blue‐Light‐Induced Stereoselective Synthesis of α‐Alkylated Amino Acid Derivatives

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

Опубликована: Март 21, 2025

Abstract A photoredox‐catalyzed decarboxylative C( sp 3 )−H alkylation of glycine derivatives, utilizing (+)/(−)‐camphorsultam as a chiral auxiliary and alkyl N ‐hydroxyphthalimide (NHP) ester radical precursor, has been developed, providing an efficient approach for the stereoselective synthesis valuable enantioenriched unnatural α ‐alkylated amino acid derivatives. The methodology operates under mild conditions, demonstrates broad substrate tolerance, exhibits excellent stereoselectivity. Preliminary mechanistic investigations indicate that reaction proceeds via pathway.

Язык: Английский

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Taming Inert B–H Bond with Low Energy Light: A Near-Infrared Light-Induced Approach to Facile Carborane Cluster-Amino Acid Coupling

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

Опубликована: Апрель 1, 2025

The selective functionalization of inert B–H bonds in carborane clusters has been a formidable challenge. Recent advances have witnessed such reactions through photoredox methods utilizing ultraviolet or visible light irradiation. However, high-energy sources often suffer from poor energy efficiency, limited substrate scope, undesired side reactions, and low scalability. Here, we present the first successful bond under low-energy near-infrared (NIR) using carborane-based electron donor–acceptor complex. Both photophysical investigations theoretical modeling reveal facile single-electron transfer cage to electron-deficient photocatalyst, generating radical NIR follow-up pathway enables direct coupling carboranes with amino acids oligopeptides, yielding diverse array carborane-functionalized oligopeptides. Beyond expanding known chemical space boron cluster derivatives, further demonstrate that imaging targeting capabilities could serve as promising multifunctional carriers for neutron capture therapy. Thus, via not only provides straightforward practical strategy synthetic chemistry but also lays foundation development next-generation boron-containing biomolecules advanced functional materials.

Язык: Английский

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Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines

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

Опубликована: Апрель 5, 2025

Photoredox catalysis has emerged as a powerful tool for forming and breaking chemical bonds, further taking hold with its integration asymmetric catalysis. While the dual-catalytic approach led to successful examples of control stereogenic centers, axes remained underexplored. In this study, an acylimine intermediate was generated through photoredox catalysis, symmetric substrate, 2-arylresorcinol, desymmetrized aid chiral phosphoric acid Using approach, center axis were successfully controlled provide natural-product-driven compound. The origins enantioselectivity diastereoselectivity investigated density functional theory study four possible enantiodetermining transition states. Consequently, first total syntheses ring-contracted naphthylisoquinoline alkaloid ancistrobrevolines A B accomplished concisely. This provides not only novel methodology strategy synthesize alkaloids but also direction advance catalytic research synthesis studies.

Язык: Английский

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Controllable Radical Reactions of 1,3-Dienes with Light

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 7749 - 7779

Опубликована: Апрель 25, 2025

Язык: Английский

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