Research progress on transition-metal-free C–N bonds cleavage of amides in the synthesis of ketones DOI
Yanlong Luo

Scientia Sinica Chimica, Год журнала: 2022, Номер 53(2), С. 129 - 144

Опубликована: Окт. 20, 2022

Amides compounds have a wide range of application, and many transforming strategies been reported. Transition metals-catalyzed non-decarbonylative cross-coupling reaction amides has gained considerable attention due to low cost, high efficiency, good compatibility functional groups. The reactions following disadvantages the inherent nature catalytic system: expensive catalysts, complex ligands, cocatalysts trace metals residues. transition-metal-free amide activation for synthesis ketones avoid above problems with efficiency simple treatment. From perspective sustainable development, development strategy without transition great significance. In this paper, by C–N bond cleavage were reviewed. main contents as follows: (1) direct addition alkali metal/alkaline-earth metal reagents amides; (2) Brønsted base-promoted alkanes activated groups; (3) based on strategy; (4) acid-promoted Friedel-Crafts acylation amide; (5) Lewis between alkyl ketone. This review provides inspiration subsequent economic green reaction.

Язык: Английский

A ruthenium catalyzed Dolye–Kirmse rearrangement reaction of sulfoxonium ylides with sulfides or selenides DOI

Yingdi Hao,

Jiao Liang,

Zhiqian Lin

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(16), С. 4038 - 4042

Опубликована: Янв. 1, 2023

A ruthenium-catalyzed Dolye–Kirmse rearrangement reaction of sulfoxonium ylides to afford sulfide- or selenide-containing compounds has been developed.

Язык: Английский

Процитировано

6

Catalyst-free activation of N–C(O) Amide bonds – efficient cascade synthesis of N-acyl thiocarbamides in batch and continuous-flow DOI
Karthick Govindan, Nian‐Qi Chen, Wei‐Yu Lin

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(9), С. 5187 - 5193

Опубликована: Янв. 1, 2024

We developed, a sustainable approach for the direct synthesis of activated amides ( N -acyl saccharin) into divergent thiocarbamide derivatives using thiocyanate salts and 2-MeTHF as green solvent.

Язык: Английский

Процитировано

2

Extended Corey–Chaykovsky reactions: transformation of 2-hydroxychalcones to benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans DOI
Alexander A. Fadeev, Антон С. Макаров, Оlga А. Ivanova

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 9(3), С. 737 - 744

Опубликована: Дек. 14, 2021

We report the divergent synthesis of benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans using concept extended Corey–Chaykovsky reactions.

Язык: Английский

Процитировано

11

Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling DOI Creative Commons
Chengwei Liu, Michal Szostak

SynOpen, Год журнала: 2023, Номер 07(01), С. 88 - 101

Опубликована: Фев. 14, 2023

Abstract This Graphical Review provides an overview of amide bond activation achieved by selective oxidative addition the N–C(O) acyl to transition metals and nucleophilic addition, resulting in decarbonylative coupling, together with key mechanistic details pertaining distortion underlying this reactivity manifold.

Язык: Английский

Процитировано

4

Synthesis of Sulfo(xo)nium Diacylmethylides DOI

Duo Fu,

Jiaxi Xu

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(27)

Опубликована: Апрель 29, 2024

Abstract Sulfo(xo)nium diacylmethylides (sulfur ylides) are simple, stable, readily prepared, and versatile synthons. Compared with the sulfo(xo)nium monoacylmethylides, they can be compatible more rigorous reaction conditions showcase unique characteristics due to their excellent stability. This concept article provides an account for syntheses of diacylmethylides, including utilization active methylene compounds, carbene precursors, electron‐deficient alkynes as substrates, discussions on substrate scopes, proposed mechanisms, selected product examples, applications. Challenges further exploration prospect in future also suggested.

Язык: Английский

Процитировано

1

Direct synthesis of α-functionalized amides via heteroatom–hydrogen insertion reactions using amide-sulfoxonium ylides DOI Creative Commons

Haiting Wu,

Yougen Xu,

Lin An

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Ноя. 25, 2024

α-Functionalized Si-, Ge-, B-, Se-, and S-amide moieties are present in many medicinally active molecules, but their synthesis remains challenging. Here, we demonstrate a high-throughput using amide-sulfoxonium ylides as carbene precursors Si-H, Ge-H, B-H, Se-H, S-H insertion reactions to target wide range of α-silyl, α-geryl, α-boryl, α-selenyl, α-sulfur (hetero)amides. The process is featured simple operation, mild conditions, broad substrate scope, high functional group compatibility, excellent chemoselectivity. Both experimental computational studies conducted explore the mechanisms underlying formation C-Si/Ge/B/Se/S bond. This research highlights use highly selective X-H with ylide-derived carbenes, paving way for preparation diverse organosilane, organogermane, organoboron, organoselenium, organosulfur compounds from accessible bench-stable precursors.

Язык: Английский

Процитировано

1

Rhodium(III)-Catalyzed Redox-Neutral [4 + 1]-Annulation of Unactivated Alkenes with Sulfoxonium Ylides DOI

Pinki Sihag,

Masilamani Jeganmohan

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(16), С. 11073 - 11089

Опубликована: Авг. 10, 2022

A novel methodology for redox-neutral [4 + 1] annulation of unactivated alkenes with sulfoxonium ylides leads to the synthesis a diverse library indanone compounds. The developed reaction was found be highly versatile due its compatibility various functionalized sensitive functional groups as well substituted ylides. Further, multiple transformations such ring-expansion, reduction, aldol condensation, and Wittig were carried out indanones. Using this way, useful cyclic heterocycles indene, dihydroisocoumarin, 1-indanilidene prepared in single step. possible mechanism supported by deuterium labeling studies, competitive kinetic isotopic studies.

Язык: Английский

Процитировано

5

The [4+1] cyclization reaction of 2-hydroxylimides and trimethylsulfoxonium iodide for the synthesis of 3-amino-2,3-dihydrobenzofurans DOI
Zhongxue Fang, Yujie Zhang, Yongsheng Guo

и другие.

New Journal of Chemistry, Год журнала: 2022, Номер 46(38), С. 18124 - 18127

Опубликована: Янв. 1, 2022

The [4+1] cyclization reaction of 2-hydroxylimides and trimethylsulfoxonium iodide was investigated.

Язык: Английский

Процитировано

5

Fe(iii)-catalysed selective C–N bond cleavage of N-phenylamides by an electrochemical method DOI Creative Commons
Yiwen Xu, Yang Long,

Runyou Ye

и другие.

RSC Advances, Год журнала: 2022, Номер 12(37), С. 24217 - 24221

Опубликована: Янв. 1, 2022

An Fe( iii )-catalysed transformation of secondary N -phenyl substituted amides to primary by an electrochemical method is developed.

Язык: Английский

Процитировано

4

1,3‐Diketone‐Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides DOI

Myeong Seong Park,

Karthik Rajan Rajamanickam,

Kwang Ho Song

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(12)

Опубликована: Окт. 10, 2023

Abstract Symmetrical aryl imides are synthesized from the reaction of activated amides such as N ‐phenyl‐ ‐tosyl benzamides. The amine source is provided by lithium hexamethyldisilazide (LiHMDS), and a 1,3‐diketone mediates generation ‐acyl donor , ‐bis(trimethylsilyl)amide. Various symmetrical thus formed in moderate to good yields.

Язык: Английский

Процитировано

2