Photochemical Wolff Rearrangement Initiated Generation and Subsequent α-Chlorination of C1 Ammonium Enolates DOI Creative Commons

David Weinzierl,

Magdalena Piringer,

Paul Zebrowski

и другие.

Organic Letters, Год журнала: 2023, Номер 25(17), С. 3126 - 3130

Опубликована: Апрель 25, 2023

The enantioselective synthesis of α-chlorinated carboxylic acid esters with er up to 99:1 and yields 82% was achieved via a one-pot multistep protocol starting from α-diazoketones. This process proceeds photochemical Wolff rearrangement, trapping the generated ketene chiral Lewis base catalyst, subsequent α-chlorination, final nucleophilic displacement bound catalyst. obtained products were successfully utilized for stereospecific reactions N- S-nucleophiles.

Язык: Английский

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI
Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Год журнала: 2024, Номер 124(11), С. 7214 - 7261

Опубликована: Май 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Язык: Английский

Процитировано

66

Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(48), С. 7346 - 7360

Опубликована: Янв. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Язык: Английский

Процитировано

48

Layer-by-layer designer nanoarchitectonics for physical and chemical communications in functional materials DOI Creative Commons
Katsuhiko Ariga, Jingwen Song, Kohsaku Kawakami

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(16), С. 2152 - 2167

Опубликована: Янв. 1, 2024

In nanoarchitectonics approaches, rational physical and chemical communications will lead to the development of more advanced functional materials. Layer-by-layer assembly can be a powerful tool for this purpose, as exemplified in feature paper.

Язык: Английский

Процитировано

28

Advances in heterocycle synthesis through photochemical carbene transfer reactions DOI
Ziyi Xie, Jun Xuan

Chemical Communications, Год журнала: 2024, Номер 60(16), С. 2125 - 2136

Опубликована: Янв. 1, 2024

In this feature article, we focus on the photochemical strategy for construction of heterocyclic skeletons, specifically highlighting methods that employ visible light-promoted carbene transfer reactions.

Язык: Английский

Процитировано

22

Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter DOI
Hua Zhang,

Zheyuan Wang,

Zirui Wang

и другие.

ACS Catalysis, Год журнала: 2022, Номер 12(9), С. 5510 - 5516

Опубликована: Апрель 25, 2022

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction enantioenriched 1,4-dicarbonyl compounds a quaternary carbon center. Combining visible light and Brønsted acid catalyst, chiral were achieved in good yields high enantioselectivities by photochemical transfer protocol.

Язык: Английский

Процитировано

43

Photochemical Synthesis of Succinic Ester-Containing Phenanthridines from Diazo Compounds as 1,4-Dicarbonyl Precursors DOI

Hai‐Bing Ye,

Xu-Yu Zhou,

Lei Li

и другие.

Organic Letters, Год журнала: 2022, Номер 24(32), С. 6018 - 6023

Опубликована: Авг. 10, 2022

We disclosed herein a straightforward photochemical method for the construction of phenanthridines containing synthetically useful succinate unit. The reaction occurred under visible-light irradiation with cheap eosin Y Na as photoredox catalyst and diazo compound precursor. Under optimal conditions, wide range were obtained in moderate to good yields. Note that units final heterocycles could be easily transformed into many valuable structures, such γ-butyrolactone, dihydrofuran-2(3H)-one, tetrahydrofuran. Mechanistic experiments performed support proposed mechanism.

Язык: Английский

Процитировано

43

Visible Light‐Mediated Cyclopropanation: Recent Progress DOI

Ze‐Le Chen,

Yang Xie, Jun Xuan

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(44)

Опубликована: Окт. 21, 2022

Abstract Cyclopropanes are one of the most important strained rings existing in various pharmaceutical products and secondary metabolites. They also widely used total synthesis natural products, medicinal chemistry, materials science. In past years, photochemical cyclopropanation has been gradually developed as a robust attractive synthetic method to prepare diverse cyclopropane backbones. this review, we summarize recent advances visible light‐mediated synthesis, especially using carbene transfer strategy photocatalytic radical reactions.

Язык: Английский

Процитировано

40

Photoinduced Palladium-Catalyzed 1,2-Difunctionalization of Electron-Rich Olefins via a Reductive Radical-Polar Crossover Reaction DOI
Hao Fang, Claire Empel, Iuliana Atodiresei

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(9), С. 6445 - 6451

Опубликована: Апрель 25, 2023

Palladium-catalyzed cross-coupling reactions belong to the most important transformations for construction of C–C or C-heteroatom bonds. More recently, photochemical activation palladium complexes emerged as a key strategy leverage catalysis at room temperature beyond scope conventional chemistry. Herein, we report on photoinduced palladium-catalyzed 1,2-difunctionalization reaction electron-rich olefins. Mechanistic experiments and computational studies reveal that this proceeds via addition an alkyl radical, followed by oxidation radical intermediate access carbocation intermediates, which are inaccessible classic thermal conditions. The can then be applied variety secondary C–N bond-forming reactions. This now allows general approach toward densely functionalized unsymmetric 1,1-bis(heterocyclyl)alkanes.

Язык: Английский

Процитировано

27

Visible-Light Photocatalyzed C3–H Alkylation of 2H-Indazoles/Indoles with Sulfoxonium Ylides via Diversified Mechanistic Pathways DOI
Altman Yuzhu Peng, Yujing Wang, Kaifeng Wang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(2), С. 1193 - 1204

Опубликована: Янв. 9, 2024

Herein, the C3–H alkylation of 2H-indazoles and indoles with sulfoxonium ylides is developed under visible-light photocatalysis. This protocol employs easily accessible reagents, a wide range 2H-indazoles, indoles, are suitable for this reaction to afford desired products benign conditions. Synergistic experimental computational studies suggest that involving photocatalysis could proceed via different mechanistic pathways. For C3-alkylation triplet energy transfer pathway proposed quenching excited photocatalyst. Subsequently, formed state undergo radical attack on C═S moiety ylides. After dissociation DMSO 1,2-H migration, final product be yielded. However, such not applicable indoles. Instead, converted C-centered in presence KH2PO4 photoredox The can C3-site thus lead

Язык: Английский

Процитировано

13

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

и другие.

Chemical Society Reviews, Год журнала: 2024, Номер 53(10), С. 4926 - 4975

Опубликована: Янв. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Язык: Английский

Процитировано

13