Photoredox-Mediated Radical Addition/Cyclization To Construct Benzannulated 6,5-Spiroketal Glycosides DOI
Chen Li, Shouyun Yu

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 30, 2025

We herein present a green and mild photoredox strategy for constructing framework of benzannulated 6,5-spiroketal glycosides. This method employs various O-arylacetylene glycosides aryl ketone acids as the starting materials, facilitating rapid straightforward synthesis with up to 92% yields under catalytic conditions. efficient approach has potential significantly enhance molecular library carbohydrate-based pharmaceuticals.

Язык: Английский

Copper-Catalyzed 1,2-Sulfonyletherification of 1,3-Dienes DOI
Pu Chen, Lin Tian, Xiaochen Ji

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 2939 - 2944

Опубликована: Апрель 11, 2024

A selective three-component 1,2-sulfonyl etherification of aryl 1,3-dienes enabled by copper catalysis to afford biologically interesting alkenyl 1,2-sulfone ether derivatives through C–S and C–O bond formation is described. The protocol proceeds with the sulfonyl chloride alcohols under simple, mild, base-free conditions, providing a straightforward route sulfonylated allyl compounds broad functional group tolerance excellent chemo- regioselectivity. Mechanistic studies indicate that alkene difunctionalization includes key copper-mediated single-electron transfer process.

Язык: Английский

Процитировано

12

Photocatalytic Sulfonylation: Innovations and Applications DOI
Anxiang Huang,

Rui Li,

Qi‐Yan Lv

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Июль 14, 2024

Photosynthesis, converting sustainable solar energy into chemical energy, has emerged as a promising craft to achieve diverse organic transformations due its mild reaction conditions, sustainability, and high efficiency. The synthesis of sulfonated compounds drawn significant attention in the pharmaceuticals, agrochemicals, materials industries unique structure electronic properties sulfonyl groups. Over past decades, many photocatalytic sulfonylation reactions have been developed. In this review, recent advances photocatalyzed reviewed since 2020, with primary focus on discussing design mechanism.

Язык: Английский

Процитировано

11

Energy Transfer (EnT)-Mediated Stereoselective Aryl-Heterofunctionalization of Unactivated Alkynes via Radical Rearrangement DOI

Xin-Chao Meng,

Tai‐Long Pan,

Feng Yang

и другие.

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

Опубликована: Янв. 5, 2025

In this study, we present a novel catalyst-free energy transfer mediated radical rearrangement strategy for the aryl-heterofunctionalization of unactivated alkynes, leading to synthesis polyfunctional olefins with exceptional stereoselectivity. This innovative approach, driven by visible light, exemplifies green chemistry principles eliminating reliance on transition metals, external oxidants, and photocatalysts. The broad applicability our method is demonstrated through successful diverse array compounds, including vinyl sulfones, selenides, sulfides. Preliminary mechanistic insights suggest an mechanism, highlighting efficiency selectivity strategy.

Язык: Английский

Процитировано

1

Photo-induced spirocyclization of biaryl ynones with ammonium thiocyanate: access to thiocyanate-featured spiro[5,5]trienones DOI
Shiliu Chen,

Qinqin Yan,

Jie Fan

и другие.

Green Chemistry, Год журнала: 2022, Номер 25(1), С. 153 - 160

Опубликована: Ноя. 25, 2022

Photo-promoted cascade 6-exo-trig spirocyclization of biaryl ynones with NH 4 SCN was developed for the preparation various SCN-containing spiro[5,5]trienones.

Язык: Английский

Процитировано

29

Visible-Light-Induced Cascade Cyclization of 3-(2-(Ethynyl)phenyl)quinazolinones to Phosphorylated Quinolino[2,1-b]quinazolinones DOI

Fan‐Lin Zeng,

Zhi-Yang Zhang,

Pengcheng Yin

и другие.

Organic Letters, Год журнала: 2022, Номер 24(43), С. 7912 - 7917

Опубликована: Окт. 21, 2022

3-(2-(Ethynyl)phenyl)quinazolinones were designed and synthesized as a class of novel efficient skeletons for phosphorylation/cyclization reactions. Under visible light irradiation, series phosphorylated quinolino[2,1-b]quinazolinones (35 examples, up to 87% yield) first from 3-(2-(ethynyl)phenyl)quinazolinones diarylphosphine oxides by using 4CzIPN photocatalyst under mild conditions. This reaction was also applicable sunlight irradiation. Moreover, the efficiency could be significantly improved continuous-flow

Язык: Английский

Процитировано

27

Metal‐Free Visible‐light Mediated C−S Bond Formation DOI
Ashish Kumar Sahoo,

Dinabandhu Barik,

Binoyargha Dam

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июнь 26, 2023

Abstract The upsurge in interest the development of methodologies for synthesis sulfur‐containing compounds via use visible‐light has been established as a sustainable tool organic chemistry. Particularly, mediated C−S bond formation gained popularity due to its operational simplicity, minimized by‐products, easy handling, mild reaction conditions, etc. Photochemistry not only provides way synthesize complex molecules but also ability overcome many challenges which are difficult attain by conventional thermal pathways. Owing biological importance compounds, present review focused on under metal‐free conditions visible‐light. objective current is bring out unearthing collection regarding photoredox catalysis. For better understanding, categorized according mode reactions viz , difunctionalization alkenes and alkynes, C−H functionalization, radical cyclization. All each sections described with selected examples proper explanation proposed mechanism.

Язык: Английский

Процитировано

16

Recent advances in hydrogen atom transfer induced C(sp3)–H functionalizations initiated by radical addition to alkynes DOI
Yulu Zhou, Zhenyu Gu,

Yuwei Hong

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1232 - 1250

Опубликована: Дек. 28, 2023

Recent advances in HAT-induced C(sp 3 )–H functionalizations triggered by radical addition to alkynes, including 5- exo-trig , endo-trig 4- and 6- cyclization cascades, intermolecular functionalizations, are summarized.

Язык: Английский

Процитировано

15

Introducing Phenalenyl-Based Organic Lewis Acid as a Photocatalyst to Facilitate Oxidative Azolation of Unactivated Arenes DOI
Partha Pratim Sen, Sudipta Raha Roy

Organic Letters, Год журнала: 2023, Номер 25(11), С. 1895 - 1900

Опубликована: Март 9, 2023

By revealing the robust photooxidant properties of phenalenyl-based organic Lewis acid, we have introduced this moiety as an effective organophotocatalyst for oxidative azolation unactivated and feedstock arenes. In addition to its tolerance various functional groups scalability, photocatalyst was shown be promising defluorinative fluoroarenes.

Язык: Английский

Процитировано

14

Multicomponent Radical Cross‐Coupling Reaction of [1.1.1]Propellane: Synthesis of 1‐Arylthiol‐3‐Heteroaryl Bicyclo[1.1.1]pentanes † DOI
Lin Li,

Yumiao Liu,

Jian Li

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(18), С. 3112 - 3117

Опубликована: Июль 26, 2023

Abstract Herein, a visible light‐mediated multicomponent radical cross‐coupling reaction of [1.1.1]propellane with N ‐heterocycles and disulfides is described. The mild conditions enabled the installation BCP motif in wide variety compounds absence photocatalyst, additive metal catalyst, excellent functional group tolerance, This methodology opens approach for synthesis potentially bioactive 1‐arylthiol‐3‐heteroaryl bicyclo[1.1.1]pentanes moderate to good yield.

Язык: Английский

Процитировано

14

Photoinduced Radical Cyclization of 1,6‐Diynes: Rapid Access to Highly Substituted Carbocyclic and Heterocyclic Compounds DOI Open Access
Mohana Reddy Mutra,

Yu‐Ting Chen,

Jeh‐Jeng Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 1012 - 1019

Опубликована: Март 7, 2023

Abstract We have developed photoinduced sulfonyl radical‐triggered cyclization of 1,6‐dynes without metals, oxidants, or additives. During the reaction, three new bonds are formed (−SO 2 −C, C−C, and C−I/C−Se−) under mild conditions, with excellent selectivity. The conversion is temporally atomically economical easy to handle even on a gram scale. Detailed mechanistic studies showed that reaction proceeds via radical pathway. Subsequent synthetic transformations products produced various substituted compounds. Importantly, we observed an unprecedented selective C−C single bond cleavage boronic acid insertion Suzuki conditions. magnified image

Язык: Английский

Процитировано

13