Recyclable ZnIn2S4 Microspheres for Photocatalytic Azolation of N-Heterocycles DOI

Ru-Nan Wang,

Fan‐Lin Zeng,

Xiaolan Chen

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2022, Номер 10(43), С. 14212 - 14219

Опубликована: Окт. 17, 2022

A series of zinc indium sulfide (ZnIn2S4) were synthesized by solvothermal methods in different solvents. After characterizations, the ZnIn2S4 prepared ethanol (i.e., ZIS-1) showed highest photocurrent density. With ZIS-1 as a photocatalyst, direct C–H azolation N-heterocycles including quinoxalin-2(1H)-ones, quinazoline, and 2H-benzo[b][1,4]oxazin-2-ones (32 examples) was realized an air atmosphere under blue light (456 nm). More importantly, microspherical photocatalyst is stable catalytic process can be used at least five times while reactivity remains unchanged. In addition, this practical approach also applicable to some other complex molecules interest, such ibuprofen isoxepac.

Язык: Английский

Enabling Cyclopropanation Reactions of Imidazole Heterocycles via Chemoselective Photochemical Carbene Transfer Reactions of NHC-Boranes DOI

Ze‐Le Chen,

Claire Empel, Kun Wang

и другие.

Organic Letters, Год журнала: 2022, Номер 24(11), С. 2232 - 2237

Опубликована: Март 11, 2022

Herein we report a site-selective cyclopropanation of N-heterocyclic carbene (NHC)-borane complexes via photochemical transfer reactions. By subtle changes to the reaction conditions, this approach can be further extended toward difunctionalization NHC-boranes and B-H insertion reaction. Further investigations in continuous-flow applications synthetic transformations proved utility method. Theoretical calculations control experiments were performed explain observed selectivity.

Язык: Английский

Процитировано

37

Metal-free visible-light-induced multi-component reactions of α-diazoesters leading to S-alkyl dithiocarbamates DOI

Yufen Lv,

Ruisheng Liu,

Hongyu Ding

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(13), С. 3486 - 3492

Опубликована: Янв. 1, 2022

A metal-free and visible-light-promoted strategy has been developed for the synthesis of S -alkyl dithiocarbamates through multicomponent reactions α-diazoesters, amines CS 2 .

Язык: Английский

Процитировано

30

Diverse catalytic systems for nitrogen-heterocycle formation from O-acyl ketoximes DOI Open Access
Zhonghua Qu,

Tong Tian,

Guo‐Jun Deng

и другие.

Chinese Chemical Letters, Год журнала: 2022, Номер 34(1), С. 107565 - 107565

Опубликована: Май 28, 2022

Язык: Английский

Процитировано

29

Dark and Light Reactions of Carbenes─Merging Carbene Transfer Reactions with N-Heterocyclic Carbene Catalysis for the Synthesis of Hydroxamic Acid Esters DOI
Bao‐Gui Cai, Qian Li, Claire Empel

и другие.

ACS Catalysis, Год журнала: 2022, Номер 12(18), С. 11129 - 11136

Опубликована: Авг. 30, 2022

Herein, we report visible light and N-heterocyclic carbene (NHC) jointly promoted multicomponent transfer reactions. Under the optimized reaction conditions, two kinds of important hydroxamic acid esters were obtained in good yields depending on media used. The key to this success was driven by blue light-promoted generation free species fast situ formation under NHC-catalyzed conditions. mild excellent functional group tolerance, useful synthetic transformations, successful modification natural products drug molecules proved utility practicality method.

Язык: Английский

Процитировано

29

Enantioselective Photochemical Carbene Insertion into C–C and C–H Bonds of 1,3-Diketones by a Guanidine-Amide Organocatalyst DOI
Shiyang Li,

Cefei Zhang,

Guihua Pan

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(7), С. 4656 - 4666

Опубликована: Март 22, 2023

A visible-light-induced enantioselective free carbene transfer reaction of α-diazoesters with 1,3-diketones is established by utilizing a chiral bifunctional guanidine-amide organocatalyst. Selective insertion into the C–C or C–H bonds 1,3-diketone could be achieved bearing different steric hindrances. The transformations enable preparation series 1,4-diketones quaternary carbon center 2-substituted-1,3-diketones in good enantioselectivities. On basis control experiments and DFT calculation, stepwise triplet coupling pathway suggested. possible mechanism proposed to explain origin high enantioselectivities via hydrogen-bonds electrostatic interactions catalyst.

Язык: Английский

Процитировано

22

Photochemical Intermolecular Cyclopropanation Reactions of Allylic Alcohols for the Synthesis of [3.1.0]-Bicyclohexanes DOI
Chao Pei, Claire Empel, René M. Koenigs

и другие.

Organic Letters, Год журнала: 2023, Номер 25(1), С. 169 - 173

Опубликована: Янв. 5, 2023

Cyclopropane-fused lactones are highly desirable in drug and natural products synthesis. Herein, we report on a photochemical, chemoselective reaction of aryldiazoacetates with allylic alcohols that furnishes cyclopropane-fused lactone skeletons efficiently one step. The diastereoselectivity the protocol was precisely controlled, cyclopropanation via free carbene intermediate followed by transesterification constitutes series bicyclic high yield without formation ether byproducts typical O–H insertion reactions.

Язык: Английский

Процитировано

18

Emerging progress: photochemical transformation of nitroso compounds DOI

Ze‐Le Chen,

Qiangqiang Li, Armido Studer

и другие.

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Июль 17, 2024

Язык: Английский

Процитировано

7

Photocatalytic Regioselective Difunctionalization of Alkenes with Diazo Compounds and tert-Butyl Nitrite: Access to γ-Oximino Esters DOI
Yantao Liu,

Keyong Zhu,

Jingjing Zhao

и другие.

Organic Letters, Год журнала: 2022, Номер 24(37), С. 6834 - 6838

Опубликована: Сен. 8, 2022

A visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to γ-oximino esters under mild conditions. Significantly, this transformation not only shows the good compatibility nucleophilic electrophilic but also displays generating alkyl radicals that preferred addition over nitroso radicals.

Язык: Английский

Процитировано

28

Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates DOI Creative Commons
Bao‐Gui Cai,

Ye‐Peng Bao,

Chao Pei

и другие.

Chemical Science, Год журнала: 2022, Номер 13(44), С. 13141 - 13146

Опубликована: Янв. 1, 2022

Photoexcitation of the azodicarboxylates results in a radical addition reaction with diazoalkanes and formation an azomethine ylide to allow for dipolar cycloaddition nitriles give 1,2,4-triazole.

Язык: Английский

Процитировано

26

Photocatalytic Transition‐Metal‐Free Direct 3‐Acetalation of Quinoxaline‐2(1H)‐ones DOI
Chunhua Ma,

Hui Meng,

Jing Li

и другие.

Chinese Journal of Chemistry, Год журнала: 2022, Номер 40(22), С. 2655 - 2662

Опубликована: Авг. 16, 2022

Comprehensive Summary A general transition‐metal‐free visible‐light‐promoted 3‐acetalation reaction of quinoxaline‐2(1 H )‐ones was developed under mild conditions. By employing 1,2,3,5‐tetrakis(carbazol‐9‐yl)‐4,6‐dicyanobenzene (4CzIPN) as an inexpensive photocatalyst, and glyoxylic acid acetal a radical source, various acetalated were constructed in moderate to good yields. Moreover, the versatility this protocol is highlighted by successful application late‐stage modification drug molecules functionality transformations. The excellent antitumor activity product demonstrated that streamlined sustainable approach could have emerged powerful strategy for structural medicinal chemistry.

Язык: Английский

Процитировано

25