Ferrocene catalyzed carbohydroxylation of alkenes using H2O and cycloketone oxime esters DOI

Sriram Ajmeera,

Durga Golagani,

Srirama Murthy Akondi

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(42), С. 8482 - 8487

Опубликована: Янв. 1, 2023

A cyanoalkyl-hydroxylation reaction of aryl alkenes has been successfully devised, employing ferrocene as a catalyst for the addition cycloketone oxime ester and H2O across double bond alkene. This environmentally friendly approach employs solvent mixture consisting water demonstrates redox neutrality, along with exceptional regio- chemoselectivity, leading to formation diverse distal hydroxy-nitrile compounds. Moreover, this research presents noteworthy contributions in terms late-stage functionalization complex molecules offers valuable insights into mechanistic aspects reaction.

Язык: Английский

Radical reactions enabled by polyfluoroaryl fragments: photocatalysis and beyond DOI
Mikhail O. Zubkov, Alexander D. Dilman

Chemical Society Reviews, Год журнала: 2024, Номер 53(9), С. 4741 - 4785

Опубликована: Янв. 1, 2024

The review summarizes advances in the radical chemistry of polyfluorinated arenes under photocatalytic conditions. fluoroaryl fragment serves as enabling motif for reaction design and efficient generation reactive intermediates.

Язык: Английский

Процитировано

9

Cobalt-Promoted Photoredox 1,2-Amidoamination of Alkenes with N-Sulfonamidopyridin-1-ium Salts and Free Amines DOI

Liangfeng Yang,

Zhiqiang Xiong, Xuan‐Hui Ouyang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1667 - 1671

Опубликована: Фев. 21, 2024

A cobalt-promoted photoredox 1,2-amidoamination of alkenes with

Язык: Английский

Процитировано

6

Photo‐/Electrocatalytic Difunctionalization of Alkenes Enabled by C‐H Radical Functionalization DOI

Zilong Zhou,

Yin Zhang,

Peizhe Cui

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(62)

Опубликована: Авг. 10, 2024

The difunctionalization of alkenes represents a powerful tool to incorporate two functional groups into the alkene bones for increasing molecular complexity and has been widely utilizations in chemical synthesis. Upon catalysis green, sustainable, mild photo-/electrochemistry technologies, much attentions have attracted development new tactics transformations important alkane feedstocks driven by C-H radical functionalization. Herein, we summarize recent advances photo-/electrocatalytic enabled We detailedly discuss substrate scope mechanisms reactions selecting impressive synthetic examples, which are divided four sections based on final terminated step, including oxidative radical-polar crossover coupling, reductive radical-radical transition-metal-catalyzed coupling.

Язык: Английский

Процитировано

5

BF3 ⋅ OEt2 and Visible Light‐Controlled [3,3]‐ or [1,3]‐Rearrangement of Quinazolinone N−O Aryl Moieties DOI

Shumin Nie,

Li‐Jie Cheng, Chun‐Hua Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2056 - 2062

Опубликована: Фев. 29, 2024

Abstract We described a base‐promoted O ‐arylation of N3‐hydroxyl quinazolinones with diaryliodonium salts and sequential BF 3 ⋅ OEt 2 visible light‐controlled [3,3]‐ or [1,3]‐rearrangements quinazolinone N−O aryl moieties to prepare variety 2‐(quinazolin‐4‐yloxy)phenols atropisomeric 3‐(2‐hydroxyphenyl)quinazolin‐4‐ones in 44%‐75% yields 28%‐70% yields, respectively. Mechanistic studies showed that HBF 4 generated situ from Et water served as the catalyst this process aryloxyquinazolinium are vital intermediates promoting [1,3]‐rearrangements. The were found undergo solely [3,3]‐rearrangement heating whereas [1,3]‐rearrangement occurred via radical under irradiation light. This method highlights formation based on use light prompt generating quinazolinones.

Язык: Английский

Процитировано

4

Solvent-Controlled Silver Catalyzed Radical Transformation of α-Imino-Oxy Acids with Cyclic Aldimines DOI
Jingjing Wang, Yong Qin,

Ke Cui

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A silver-catalyzed cross coupling of cyclic aldimines and α-imino-oxy acids has been developed. The solvent-dependent reaction could selectively deliver either imine moiety retained nitriles or ring-opened oxonitriles in moderate yields.

Язык: Английский

Процитировано

0

Ruthenium-Catalyzed Formation of 1-Azetines via Oxidative β-Elimination from Azetidine Benzoates DOI
Dominique E. Blackmun, Michael R. Gatazka, P Chiu

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4934 - 4941

Опубликована: Март 7, 2025

Язык: Английский

Процитировано

0

Chemically revertible molecular clasps: Hydroxamic acid-mediated peptide macrocyclization and linearization DOI
Elaine Fowler, Justin Kim

Chem, Год журнала: 2024, Номер 10(2), С. 730 - 745

Опубликована: Янв. 4, 2024

Язык: Английский

Процитировано

2

Mechanochemical Conditions for Intramolecular N–O Couplings via Rhodium Nitrenoids Generated from N‐Acyl Sulfonimidamides DOI Creative Commons

Shulei Pan,

Peng Wu,

Dimitra Bampi

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Окт. 9, 2024

Abstract Starting from N ‐acyl sulfonimidamides, mechanochemically generated rhodium nitrenoids undergo intramolecular N−O couplings to provide unprecedented 1,3,2,4‐oxathiadiazole 3‐oxides in good excellent yields. The cyclization proceeds efficiently with a catalyst loading of only 0.5 mol % the presence phenyliodine(III) diacetate (PIDA) as oxidant. Neither an inert atmosphere nor additional heating is required this solvent‐free procedure. Under heat or blue light, newly formed five‐membered heterocycles function nitrene precursors reacting sulfoxides exemplified by imidation dimethyl sulfoxide.

Язык: Английский

Процитировано

2

The diacetyliminoxyl radical in oxidative functionalization of alkenes DOI
Alexander S. Budnikov, Igor B. Krylov,

Andrey V. Lastovko

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(38), С. 7758 - 7766

Опубликована: Янв. 1, 2023

The intermolecular oxime radical addition to CC bonds was observed and studied for the first time. diacetyliminoxyl proposed as a model reagent study of reactivity towards unsaturated substrates, which is important in light active development synthetic applications radicals. In present work it found that reacts with vinylarenes conjugated dienes give products, whereas unconjugated alkenes can undergo or allylic hydrogen substitution by depending on substrate structure. Remarkably, substituted high yields C-O coupling products despite significant steric hindrance, unsubstituted lower products. atypical yield dependence alkene structure explained discovered ability attack formation C-N bond instead giving side This process not expected sterically hindered due availability N-atom than O-atom.

Язык: Английский

Процитировано

4

I2 Catalyzed and TBHP/Ammonium-Promoted Conversion of Arylethanone to Nitriles via β-Scission of Iminyl Radicals DOI

Kui Zheng,

Chen Liang,

Hailong Chen

и другие.

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3935 - 3939

Опубликована: Апрель 26, 2024

Herein, we report a general I

Язык: Английский

Процитировано

1