A general approach to stereospecific Pd-catalyzed cross-coupling reactions of benzylic stereocenters DOI Creative Commons

Meruyert Binayeva,

Xinghua Ma,

Pejman Ghaemimohammadi

и другие.

Chemical Science, Год журнала: 2023, Номер 14(48), С. 14124 - 14130

Опубликована: Янв. 1, 2023

We have developed a general process for the formation of enantioenriched benzylic stereocenters via stereospecific Pd-catalyzed cross-coupling reactions tricyclohexyltin nucleophiles. This proceeds with excellent stereospecificity remarkably broad scope electrophilic coupling partners including aryl and heteroaryl halides triflates, acid chlorides, thioesters, chloroformates, carbamoyl chlorides. Thus, 1,1-diarylalkanes as well formal products asymmetric enolate arylation are readily accessed using this approach. additionally provide first demonstration Sn-selective reaction vicinal alkylborylstannane nucleophile. In these reactions, presence cyclohexyl spectator ligands on tin is essential to ensure selective transfer secondary unit from palladium.

Язык: Английский

Mechanical treated natural kapok fiber with Ep through oil-milling process for bio-based modified asphalt: Analysis of ageing resistance and Ep releasing DOI Creative Commons
Shun Chen, Wentian Wang, Xingyang He

и другие.

Case Studies in Construction Materials, Год журнала: 2025, Номер unknown, С. e04582 - e04582

Опубликована: Март 1, 2025

Язык: Английский

Процитировано

0

NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes DOI
Zhaoyang Zhang, Jiayi Yang,

Shihao Li

и другие.

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed.

Язык: Английский

Процитировано

0

Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates DOI Creative Commons
Changlei Zhu, Jiaxin Lin, Xiaoguang Bao

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 4, 2025

In recent years, amination of alkylboronates through ionic copper catalysis or boron-ate complex 1,2-metalation has been well established, but complementary radical processes remain less studied before. Herein, based on rational design, we develop several imine-type N-centered scavengers and apply them to the alkylboronates. The reaction proceeds under mild photoredox-catalyzed transition-metal-free conditions features excellent functional group tolerance. It also enables preparation a range medicinally valuable amine derivatives from natural products. Further application this reagent in C-H amination, deoxygenative decarboxylative three component trifluoromethylative/sulfonylative aminations are realized. mechanistic studies DFT calculations conducted provide detailed evidence for mechanism.

Язык: Английский

Процитировано

0

C(sp3)—H Bond Oximinylation DOI

Antuo Xu,

Junyi Li, Qiang Liu

и другие.

Acta Chimica Sinica, Год журнала: 2025, Номер 83(4), С. 390 - 390

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

A Barton nitrite ester-type remote functionalization and cyclization of N-nitrosobenzamides DOI
Tao Huang, Pan‐Feng Yuan, Kui Dong

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(18), С. 4559 - 4564

Опубликована: Янв. 1, 2023

The preparation of benzo[ d ][1,2]oxazin-1-ones from N -ethyl- -nitrosobenzamides was established via a visible-light-driven Barton reaction and subsequent nucleophilic cyclization.

Язык: Английский

Процитировано

7

Photoredox-Catalyzed Amino-Radical-Transfer-Mediated Three-Component Alkylarylation of Alkenes DOI

Di-Di Tang,

Yu‐Zhao Wang, Chenjiang Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6477 - 6481

Опубликована: Июль 23, 2024

We herein reported a novel photoredox-catalyzed three-component alkylarylation of vinyl arenes with alkylboronic pinacol esters (APEs) and cyanoarenes via radical addition/cross-coupling to construct 1,1-diarylalkanes. In this transformation, alkyl radicals were easily available by visible-light-induced oxidative N-H cleavage morpholine, which used APEs as precursor. Furthermore, protocol exhibited broad substrate scope, enabling various styrenes, APEs, cyanoarenes, well bioactive molecule derivatives.

Язык: Английский

Процитировано

2

Rongalite/Iodine-Mediated C(sp3)–H Bond Oximation and Thiomethylation Reaction of Methyl Ketones Using Copper Nitrate as the [NO] Reagent: Synthesis of Thiohydroximic Acids DOI
Miao Wang, Huiying Ren,

Xiao-Yu Pu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(37), С. 7623 - 7627

Опубликована: Янв. 1, 2024

In this work, a highly efficient rongalite/iodine-mediated oxime formation reaction for the preparation of thiohydroximic acids from methyl ketones by employing copper nitrate as [NO] reagent has been developed. Notably, participated both catalyst and mild oximation in transformation. This is facile, with broad substrate scope, especially fused ring skeleton substrates, heterocyclic acetyl-substituted natural products. Mechanistic studies revealed that might be converted into NO

Язык: Английский

Процитировано

1

Nickel/Photoredox Catalyzed Aryl‐Alkyl Cross‐Coupling with Alkyl Boronic Esters as Radical Precursors DOI Open Access
Lijun Gao,

Yi-Xuan Xin,

Peizhuo Lv

и другие.

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

Опубликована: Дек. 10, 2024

Abstract Nickel/photoredox dual catalyzed cross‐coupling of aryl halides with alkylboron compounds is one the effective methodologies for construction C(sp 2 )−C(sp 3 ) bonds. Although elegant results have been achieved by using alkyl trifluoroborates as radical precursors, generation radicals from readily available boronic esters still limited due to their high oxidation potential. We disclosed here that activation MeOLi highly efficient under photocatalysis conditions. The reaction featured a wide substrate scope, functional group tolerance, and late‐stage modification bioactive substances. In addition, method was also successfully extended acids. Experimental computational mechanistic studies indicated likely proceeds via Ni(I)‐catalyzed pathway.

Язык: Английский

Процитировано

1

Visible-Light-Induced Radical Carbon Oximation of Styrenes Using N-Nitrosoamine and Organic Halides DOI

Jinping Lan,

Xiaolong Li, Mengyu Xu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

An efficient visible-light-induced radical carbon oximation of styrenes with 1-nitrosopyrrolidine and organic halides is developed. The reaction proceeds smoothly in the absence a transition metal photocatalyst under mild conditions, producing wide range functionalized oximes moderate to good yields. Mechanistic studies reveal that involves generation nucleophilic α-amino alkyl radicals subsequent halogen atom transfer (XAT) halides.

Язык: Английский

Процитировано

1

Catalytic Aerobic Carbooximation of Alkenes Using Secondary Nitroalkanes as Both α-Nitro Alkyl Radical and Nitrogen Monoxide Sources DOI

H. S. PARK,

Soumyadeep Roy Chowdhury,

Hun Young Kim

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 25, 2024

Aerobic nitro-nitrite isomerization of secondary nitroalkanes is postulated to proceed via the intermediacy α-nitro alkyl radical, where corresponding Nef-type products, ketones, and nitrogen monoxide can be obtained as byproducts. To explore catalytic aerobic carbooximation alkenes using nitroalkanes, phase-transfer catalysis KSeCN TBAI has been developed. The current utilizes both radical sources in water without external oxidants prefunctionalized nitroalkanes.

Язык: Английский

Процитировано

1