Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade DOI
Bao‐Gui Cai,

Wei‐Zhong Yao,

Lei Li

и другие.

Organic Letters, Год журнала: 2022, Номер 24(36), С. 6647 - 6652

Опубликована: Сен. 2, 2022

A visible-light-promoted three component reaction of diazo compounds, nitriles, and carboxylic acids is reported. The utilizes acceptor-only compounds as carbene precursors nitriles carbene-trapping reagents to form the key nitrile ylides. Under optimal conditions, a wide range imide products were obtained in good excellent yields. gram-scale synthesis synthetic application isoquinoline-1,3(2H,4H)-dione derivatives further proved value this method.

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

60

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

46

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-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate DOI Open Access
Bao‐Gui Cai, Jun Xuan

Chinese Journal of Organic Chemistry, Год журнала: 2021, Номер 41(12), С. 4565 - 4565

Опубликована: Янв. 1, 2021

Carbene is one of the most important synthetic intermediates in organic synthesis.In past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development.Recently, visible light-promoted transformation diazo compounds through formation free as key intermediate begun to rise.The reaction only need light sole energy source which meets concept green chemistry.Since pioneering works developed by groups Diaves and Zhou, photo-promoted has attracted more attentions.On basis previous work, latest progress this field further improved, mainly focuses on recent new under irradiation contributions reported from Chinese research group.The future development direction, well challenges prospected.

Язык: Английский

Процитировано

66

Oxime Ether Synthesis through O–H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation DOI
Qian Li, Bao‐Gui Cai, Lei Li

и другие.

Organic Letters, Год журнала: 2021, Номер 23(17), С. 6951 - 6955

Опубликована: Авг. 12, 2021

A green and sustainable oxime ether formation method via the visible-light-promoted O–H functionalization of oximes with diazo esters is described. The reaction occurs under very mild conditions (catalyst- additive-free) a high yield functional group tolerance. When was performed cyclic as solvent (e.g., THF, 1,4-dioxane, tetrahydropyran, ect.), an interesting photochemical three-component product obtained in good yields.

Язык: Английский

Процитировано

64

Visible‐Light Photosynthesis of CHF2/CClF2/CBrF2‐Substituted Ring‐fused Quinazolinones in Dimethyl Carbonate DOI
Qingwen Gui, Fan Teng, Hao Yang

и другие.

Chemistry - An Asian Journal, Год журнала: 2021, Номер 17(1)

Опубликована: Ноя. 26, 2021

With eco-friendly and sustainable CO2 -derived dimethyl carbonate as the sole solvent, visible-light-induced cascade radical reactions have been established a green efficient tool for constructing various CHF2 /CClF2 /CBrF2 -substituted ring-fused quinazolinones.

Язык: Английский

Процитировано

59

Perovskite as Recyclable Photocatalyst for Annulation Reaction of N-Sulfonyl Ketimines DOI

Anzai Shi,

Kai Sun, Xiaolan Chen

и другие.

Organic Letters, Год журнала: 2021, Номер 24(1), С. 299 - 303

Опубликована: Дек. 16, 2021

A sustainable and cost-effective manner for the photocatalytic annulation reaction of N-sulfonyl ketimines with N-arylglycines to synthesize imidazolidine-fused sulfamidates (31 examples) by employing CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst can be simply recovered from mixture reused at least five times without an obvious reduction in its reactivity, exhibiting high economic feature.

Язык: Английский

Процитировано

58

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

39