Electrochemical oxidative radical cascade reactions for the synthesis of difluoromethylated benzoxazines

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3898 - 3902

Опубликована: Янв. 1, 2023

An efficient electrochemical synthesis of fluoroethylated benzoxazines via oxyfluoromethylation was developed. The broad applicability and general utility were tested highlighted by the substrate scope late-stage synthesis.

Язык: Английский

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Radical-mediated alkoxypolyhaloalkylation of styrenes with polyhaloalkanes and alcohols via C(sp³)–H bond cleavage

Chemical Communications, Год журнала: 2021, Номер 57(30), С. 3684 - 3687

Опубликована: Янв. 1, 2021

A radical-mediated alkoxypolyhaloalkylation of styrenes with polychloroalkanes and alcohols for the facile synthesis complex polyhaloalkanes excellent functional-group compatibility a broad substrate scope.

Язык: Английский

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Metal-Catalyst-Free Radical Cyclization of 1,6-Enynes for the Selective and Switchable Synthesis of Lactams in Water

ACS Sustainable Chemistry & Engineering, Год журнала: 2022, Номер 10(18), С. 6057 - 6062

Опубликована: Апрель 27, 2022

Three types of novel radical cyclization 1,6-enynes with sulfonyl hydrazides have been presented, which provided convenient synthetic approaches for accessing five-membered cyclic lactams, lactams containing C–I bond, and six-membered lactams. Notably, these transformations are implemented in metal-catalyst-free systems, three classes important lactam derivatives were synthesized selectivity controllability from the same substrate using water as green solvent.

Язык: Английский

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Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines

Chinese Journal of Organic Chemistry, Год журнала: 2023, Номер 43(12), С. 4213 - 4213

Опубликована: Янв. 1, 2023

Benzoxazines are important motif in pharmaceuticals and functional molecules.A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed.In present protocol, a series olefinic amides can be transferred to difluoroethylated via oxydifluoromethylation CF2HSO2Na as difluoromethylating reagent, which is easily operated good group tolerant.

Язык: Английский

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Iron-Mediated Bromocyclization of Olefinic Amides for the Synthesis of Bromobenzoxazines

Synthesis, Год журнала: 2024, Номер 56(19), С. 2993 - 3000

Опубликована: Июнь 5, 2024

Abstract An iron-mediated bromination/cyclization for the synthesis of bromobenzoxazines from olefinic amides has been successfully developed. In this protocol, simple iron salt FeBr3 was employed as a bromination reagent, giving bromobenzoxazine products in moderate to excellent yields. This methodology features good functional group tolerance, gram-scale synthesis, and green reaction conditions by use air terminal oxidant. Preliminary mechanistic studies suggest that free radical pathway is involved.

Язык: Английский

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Highly efficient and fast synthesis of di-iodinated succinimide derivatives from 1,6-enyne and I₂ under air at room temperature

Green Chemistry, Год журнала: 2022, Номер 24(20), С. 8021 - 8028

Опубликована: Янв. 1, 2022

A metal-free, additive-free, and practical method for the synthesis of diiodinated succinimide derivatives has been achieved under mild conditions.

Язык: Английский

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Electrochemical oxidative cyclization of N-allylamides for the synthesis of CF₃-containing benzoxazines and oxazolines

RSC Advances, Год журнала: 2024, Номер 14(1), С. 154 - 159

Опубликована: Янв. 1, 2024

The introduction of trifluoromethyl (-CF3) groups into compounds is a common synthetic strategy in organic chemistry. Commonly used methods for introducing are limited by harsh reaction conditions, low regioselectivity, or the need excess reagents. In this study, facile electrochemical oxidative and radical cascade cyclization N-(2-vinylphenyl)amides synthesis CF3-containing benzoxazines oxazolines was obtained. This sustainable protocol features inexpensive durable electrodes, wide range substrates, diverse functional group compatibility under transition-metal-free, external-oxidant-free, additive-free can be applied an open environment.

Язык: Английский

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Green Tandem [5C + 1C] Cycloaromatization of α-Alkenoyl Ketene Dithioacetals and Nitroethane in Water: Eco-Friendly Synthesis of Ortho-Acylphenols

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 2985 - 2996

Опубликована: Фев. 8, 2022

For the first time, an eco-friendly and sustainable tandem [5C + 1C] cycloaromatization of α-alkenoyl ketene dithioacetals nitroethane in water for efficient synthesis ortho-acylphenols was reported. In refluxing water, a range smoothly underwent Michael addition/cyclization/aromatization reactions presence 2.0 equivalents DBU to provide various excellent yields. The green approach not only avoided use harmful organic solvents, which could result serious environmental safety issues, but also exhibited fascinating features such as good substrate scope, yields, simple purification desired products, ease scale-up, reusable aqueous medium.

Язык: Английский

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Synthesis of Polycyclic Quinazolinones through C(sp³)−H Functionalization of Inert Alkanes or Visible‐Light‐Promoted Oxidation Decarboxylation of N‐Hydroxyphthalimide Esters

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(35)

Опубликована: Май 20, 2022

Abstract Two novel C(sp 3 )−H functionalization of inert alkanes and visible‐light promoted oxidation decarboxylation N ‐hydroxyphthalimide (NHP) esters to access polycyclic quinazolinones have been described. These methods do not involve metal catalysts are carried out in water or water/DMSO media. The wide substrate scope, even including the seven‐membered ring under mild reaction conditions, demonstrate practicability these strategies.

Язык: Английский

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Uncatalyzed diastereoselective synthesis of alkyliminofurochromone-derived benzylmalononitriles via a three-component cascade reaction: competition between Diels–Alder cycloaddition and Michael addition

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(11), С. 2517 - 2525

Опубликована: Янв. 1, 2021

Three new chemical bonds and three stereogenic centres one heterocyclic ring were assembled stereoselectively in a convenient high atom-economy one-pot operation.

Язык: Английский

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