Zinc‐Mediated Radiosynthesis of Unprotected Fluorine‐18 Labelled α‐Tertiary Amides DOI Creative Commons
Jay S. Wright,

Richard Ma,

Eric Webb

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(2)

Опубликована: Ноя. 28, 2023

This report describes the development of a Zn(OTf)2 -mediated method for converting α-tertiary haloamides to corresponding fluorine-18 labelled fluoroamides with no-carrier-added [18 F]tetramethylammonium fluoride. 1,5,7-Triazabicyclo[4.4.0]dec-5-ene is an essential additive achieving high radiochemical conversion. Under optimised conditions, radiofluorination proceeds at sterically hindered tertiary sites in conversions, yields, and purities. has been successfully automated applied access >200 mCi (>7.4 GBq) several model radiofluorides. Mechanistic studies led new, nucleophilic C-H process using N-sulphonyloxyamide substrates.

Язык: Английский

Copper-catalysed enantioconvergent alkylation of oxygen nucleophiles DOI
Caiyou Chen, Gregory C. Fu

Nature, Год журнала: 2023, Номер 618(7964), С. 301 - 307

Опубликована: Март 30, 2023

Язык: Английский

Процитировано

50

Photoinduced copper-catalysed deracemization of alkyl halides DOI
Feng Zhong, Renhe Li, Binh Khanh

и другие.

Nature, Год журнала: 2025, Номер 640(8057), С. 107 - 113

Опубликована: Апрель 2, 2025

Язык: Английский

Процитировано

3

Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins DOI
Yi Liu, Sophie G. Bender,

Damien Sorigue

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(11), С. 7191 - 7197

Опубликована: Март 5, 2024

Photoenzymatic intermolecular hydroalkylations of olefins are highly enantioselective for chiral centers formed during radical termination but poorly selective set in the C–C bond-forming event. Here, we report evolution a flavin-dependent "ene"-reductase to catalyze coupling α,α-dichloroamides with alkenes afford α-chloroamides good yield excellent chemo- and stereoselectivity. These products can serve as linchpins synthesis pharmaceutically valuable motifs. Mechanistic studies indicate that formation occurs by exciting charge-transfer complex templated protein. Precise control over orientation molecules within potentially accounts observed The work expands types motifs be prepared using photoenzymatic catalysis.

Язык: Английский

Процитировано

16

The Fascinating Chemistry of α‐Haloamides DOI Creative Commons
Anna Fantinati, Vinicio Zanirato, Paolo Marchetti

и другие.

ChemistryOpen, Год журнала: 2020, Номер 9(2), С. 100 - 170

Опубликована: Янв. 13, 2020

The aim of this review is to highlight the rich chemistry α-haloamides originally mainly used discover new C-N, C-O and C-S bond forming reactions, later widely employed in C-C cross-coupling reactions with C(sp3), C(sp2) C(sp) coupling partners. Radical-mediated transformations bearing a suitable located unsaturated has proven be straightforward alternative access diverse cyclic compounds by means either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On other hand, cycloadditions α-halohydroxamate-based azaoxyallyl cations have garnered significant attention. Moreover, view important role life materials science difluoroalkylated compounds, wide range catalysts been developed for efficient incorporation difluoroacetamido moieties into activated as well unactivated substrates.

Язык: Английский

Процитировано

40

Diastereoselective [3 + 1] Cyclization Reaction of Oxindolyl Azaoxyallyl Cations with Sulfur Ylides: Assembly of 3,3′-Spiro[β-lactam]-oxindoles DOI
Hai‐Jun Leng, Qing‐Zhu Li, Peng Xiang

и другие.

Organic Letters, Год журнала: 2021, Номер 23(4), С. 1451 - 1456

Опубликована: Фев. 1, 2021

Oxindoles and β-lactams are attractive structural motifs because of their unique biological importance. However, the fusion two moieties featuring 3,3′-spirocyclic scaffolds is a challenging task in organic synthesis. Herein we designed novel type oxindole-based azaoxyallyl cation synthons, which could readily participate [3 + 1] cyclization with sulfur ylides. With this protocol, collection 3,3-spiro[β-lactam]-oxindoles were facilely produced up to 94% yield perfect diastereoselectivity.

Язык: Английский

Процитировано

30

Divergent functionalization of alkenes enabled by photoredox activation of CDFA and α-halo carboxylic acids DOI Creative Commons
Rahul Giri, Egor S. Zhilin, Dmitry Katayev

и другие.

Chemical Science, Год журнала: 2024, Номер 15(27), С. 10659 - 10667

Опубликована: Янв. 1, 2024

The direct activation of α-halo carboxylic acids using visible-light-mediated photoredox catalysis facilitates the formation bifunctional radical intermediates, allowing reactivity toward olefins to be fine-tuned by varying solvent system.

Язык: Английский

Процитировано

5

Heteroannulation of Arynes with α-Bromodifluorohydroxamates: An Efficient and General Approach to Access 2,2-Difluoro Indoxyls DOI

Deeksha,

Ritesh Singh

Organic Letters, Год журнала: 2024, Номер 26(27), С. 5682 - 5688

Опубликована: Июнь 27, 2024

Herein, we report the first general approach to access

Язык: Английский

Процитировано

4

Potential antiviral and anticancer effect of imidazoles and bridgehead imidazoles generated by HPV-Induced cervical carcinomas via reactivating the P53/ pRb pathway and inhibition of CA IX DOI
Aisha Y. Hassan, Samiha A. El‐Sebaey, Moshira A. El Deeb

и другие.

Journal of Molecular Structure, Год журнала: 2021, Номер 1230, С. 129865 - 129865

Опубликована: Янв. 2, 2021

Язык: Английский

Процитировано

21

Controllable Hydrodebromination of Tribromomethyl Groups via Lewis Base–Borane-Mediated Ionic and Radical Pathways DOI
Feng‐Lian Zhang, Yi‐Feng Wang, Yan Liu

и другие.

Synthesis, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Abstract Compounds bearing mono- and dibromomethyl groups are extensively utilized in synthetic medicinal chemistry. In this regard, selective debromination of readily or easily accessible tribromomethyl compounds offers a direct efficient method to access those two moieties. work, we introduced Lewis base–borane-mediated hydrodebromination via ionic radical pathway. Using 4-(dimethylamino)pyridine–borane (DMAP-BH3) as hydride donor, monohydrodebromination was achieved nucleophilic substitution by hydride, delivering groups. On the other hand, treatment with an N-heterocyclic carbene–borane (NHC-BH2CN) boryl precursor presence dilauroyl peroxide (DLP) initiator afforded monobromomethyl through consecutive bromine atom abstractions cleave C–Br bonds. Various group acetamides acetates were applied developed protocol, showcasing good functional tolerance broad substrate scope.

Язык: Английский

Процитировано

0

Visible-Light-Driven Catalytic Dehalogenation of Trichloroacetic Acid and α-Halocarbonyl Compounds: Multiple Roles of Copper DOI Creative Commons

Abigail J. Thillman,

Erin C. Kill,

Alexander N. Erickson

и другие.

ACS Catalysis, Год журнала: 2025, Номер 15(5), С. 3873 - 3881

Опубликована: Фев. 19, 2025

Herein, we report the reaction development and mechanistic studies of visible-light-driven Cu-catalyzed dechlorination trichloroacetic acid for highly selective formation monochloroacetic acid. Visible-light-driven transition metal catalysis via an inner-sphere pathway features dual roles species in photoexcitation substrate activation steps, a detailed understanding their is crucial further light-driven catalysis. This catalytic method, which environmentally desired ascorbic as hydrogen atom source water/ethanol solvent, can be applied to dehalogenation variety halocarboxylic acids amides. Spectroscopic, X-ray crystallographic, kinetic have revealed mechanism copper photoexcitation, thermal first C–Cl bond, excited-state second bond chlorine transfer.

Язык: Английский

Процитировано

0