Selective Oxyfunctionalization of Benzylic C–H with No Solvent DOI
Miao Tian, Jinya Li, Quansheng Mou

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16645 - 16652

Опубликована: Ноя. 6, 2024

The direct selective oxyfunctionalization of C–H into C═O represents a highly useful, yet challenging, synthetic methodology. Herein, one-step benzylic aryl ketone, with no overoxidation the −OH functional group, is reported through mechanochemistry. substrate scope also tolerant wide range different groups, providing particularly sustainable widely adaptable route for synthesis ketones, which represent both classic precursor and useful strategy lignin monomer valorization. A series mechanistic spectroscopic investigations were conducted to shed light on unique over selectivity, opening up new avenues oxidation chemistry.

Язык: Английский

Thermocontrolled Radical Nucleophilicity vs Radicophilicity in Regiodivergent C–H Functionalization DOI

Buddhadeb Pal,

Prasenjit Mal

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 8, 2025

The temperature-dependent switching behavior of the saccharin radical is demonstrated, enabling regiodivergent C3–H and C7–H functionalization quinoxalin-2(1H)-ones. was generated through N–Br bond cleavage in N-bromosaccharin (NBSA) observed to transition between radicophile roles. At −10 °C, it utilized as a radicophile, resulting 100% C3-amination, while at +35 acted radical, leading exclusive C7-bromination. Radical nucleophilicity controlled by temperature modulation.

Язык: Английский

Процитировано

2
Mechanochemical Copper-Catalyzed Synthesis of NH-Sulfonimidamides by Oxidative Amination of Primary Sulfinamides DOI
Peng Wu,

Ling Li,

Yijie Hu

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(43), С. 15875 - 15880

Опубликована: Окт. 15, 2024

A mechanochemical copper-catalyzed oxidative amination of primary sulfinamides has been developed, leading to NH-sulfonimidamides in moderate good yields under solvent-free conditions. Air serves as a terminal oxidant without the need for external additives. The obtained products could be readily converted into both acyclic and cyclic sulfonimidamide derivatives. This approach demonstrates considerable ecological benefits compared solvent-based methods.

Язык: Английский

Процитировано

4
Intermolecular amination of Ethyl Benzo ylacetate via photocatalytic nitrene transfer reactions DOI
Yujing Guo, Yifan Guo,

Luyao Ding

и другие.

Organic Chemistry Frontiers, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This study reports a photocatalytic nitrene transfer reaction of 1,3-dicarbonyl. A broad range substrates and iodinanes are shown, enabling direct C–H functionalization without the need for pre-formed nucleophilic enolate equivalents.

Язык: Английский

Процитировано

0
Direct Synthesis of Organothianthrenium Salts under Ball Milling Conditions DOI
Pan Gao,

Ya Yang,

Xinting Fan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер 23(19), С. 4636 - 4640

Опубликована: Янв. 1, 2025

The solvent-free mechanochemical method enables efficient synthesis of diverse organothianthrenium salts via ball-milling technique, eliminating the need for hazardous reactants, inert atmosphere, and complex reaction setups.

Язык: Английский

Процитировано

0
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
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, 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

0
TMEDA-enabled regioselective sulfenylation of unprotected N-heterocycles via electrochemical sulfinyl radical generation DOI

Qiang Zhong,

Xinru Jiang, Hui Gao

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

An electrochemical sulfenylation of unprotected N -heterocycles with a wide range commercially available arylsulfonyl chlorides was developed.

Язык: Английский

Процитировано

0
Rapid and chemoselective imidation of sulfides in aqueous buffer enabled by a novel guanidine-derived N-O reagent DOI

Hanzheng Li,

Long Xu, Jiajia Dong

и другие.

Science China Chemistry, Год журнала: 2024, Номер 67(6), С. 1929 - 1934

Опубликована: Май 11, 2024

Язык: Английский

Процитировано

0
Efficient Synthesis of (S)-Aromatic Epoxides by Coupling Mechanochemical Synthesis and Biocatalysis Technology DOI
Ling Jiang,

Hailing Yang,

Qiong Xiao

и другие.

ACS Sustainable Chemistry & Engineering, Год журнала: 2024, Номер 12(37), С. 13774 - 13782

Опубликована: Сен. 3, 2024

(S)-aromatic epoxides are of great importance in the production pharmaceuticals and biologically active natural products. Consequently, developing efficient, ecofriendly, economical methods for continues to be tremendous interest organic synthesis. Herein, we report a novel protocol efficient synthesis by coupling mechanochemical biocatalysis from commercially available cheap materials. The first step process is halogenation aromatic ketones with N-halosuccinimides (NXS) under ball-milling conditions form α-haloaromatic ketones. This followed one-pot asymmetric bioreduction–cyclization sequence affording various good yields, which pure enough without further purification. Compared traditional chemical approaches, this mechano-biocatalytic has prominent advantages, including inexpensive starting materials, short reaction time, simplicity operation, environmental benignity, broad substrate spectrum, excellent enantioselectivities, easy isolation

Язык: Английский

Процитировано

0
Selective Oxyfunctionalization of Benzylic C–H with No Solvent DOI
Miao Tian, Jinya Li, Quansheng Mou

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16645 - 16652

Опубликована: Ноя. 6, 2024

The direct selective oxyfunctionalization of C–H into C═O represents a highly useful, yet challenging, synthetic methodology. Herein, one-step benzylic aryl ketone, with no overoxidation the −OH functional group, is reported through mechanochemistry. substrate scope also tolerant wide range different groups, providing particularly sustainable widely adaptable route for synthesis ketones, which represent both classic precursor and useful strategy lignin monomer valorization. A series mechanistic spectroscopic investigations were conducted to shed light on unique over selectivity, opening up new avenues oxidation chemistry.

Язык: Английский

Процитировано

0