Recent Progress of Electron‐Withdrawing‐Group‐Tethered Arenes Involved Asymmetric Nucleophilic Aromatic Functionalizations DOI
Yanli Li, Kai‐Kai Wang, Xiao‐Long He

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(21), С. 3630 - 3650

Опубликована: Окт. 3, 2022

Abstract Electron‐withdrawing groups (EWG) have emerged as a powerful tool for the activation of various arenes to promote nucleophilic dearomative additions construction complicated chiral cyclic structures under asymmetric catalytic systems. Nitro‐indoles, nitro‐benzofurans/benzothiophenes, and related nitro‐heteroarenes are widely applied in reaction with nucleophiles construct enantioenriched polycyclic skeletons via dearomatization process. Meanwhile, electron‐deficient azo‐group nitroso‐group an alternative arenes, which enable formal aromatic arylations electrophilic aromatics novel biaryl atropisomers. Besides, azo‐naphthanenes served dipolar surrogates dipolarophiles proceed cycloadditions skeletons. The EWG‐tethered arene has proven be versatile protocol structurally diversified backbones. This review summarizes latest progress involved transformations organo‐ or transition metal catalysis. magnified image

Язык: Английский

Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives DOI Open Access

Feng‐Tao Sheng,

Jing‐Yi Wang, Wei Tan

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(23), С. 3967 - 3998

Опубликована: Янв. 1, 2020

This review summarizes the progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives and their applications total synthesis natural products, gives some insights into challenging issues this research field.

Язык: Английский

Процитировано

216

Recent Advances in the Catalytic Functionalization of “Electrophilic” Indoles DOI

Alessandro Cerveri,

Marco Bandini

Chinese Journal of Chemistry, Год журнала: 2019, Номер 38(3), С. 287 - 294

Опубликована: Дек. 12, 2019

When “dark” is bright : the scarcely explored electrophilic profile of indolyl core ( dark‐side ) continues to inspire developments in organic synthesis by means new catalytic methodologies. Recent advancements field enabled molecular diversity and complexity be effectively realized within heterocyclic chemistry.

Язык: Английский

Процитировано

97

Reactivity of 3-nitroindoles with electron-rich species DOI

Batoul Rkein,

Antoine Bigot,

Léo Birbaum

и другие.

Chemical Communications, Год журнала: 2020, Номер 57(1), С. 27 - 44

Опубликована: Ноя. 25, 2020

3-Nitroindoles behave as electron-poor aromatic compounds and react toward a number electron-rich species. This feature article presents an overview of this reactivity, mainly in (formal) dearomatizing cycloaddition reactions.

Язык: Английский

Процитировано

57

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides DOI
Jian‐Qiang Zhao, Zhou Shun, Lei Yang

и другие.

Organic Letters, Год журнала: 2021, Номер 23(21), С. 8600 - 8605

Опубликована: Окт. 21, 2021

An enantioselective dearomative 1,3-dipolar cycloaddition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides with a bifunctional hydrogen-bonding thiourea catalyst was established, giving polyheterocyclic compounds in excellent results (up to 99% yield, >20:1 dr for all cases up ee). The enantioselectivity could be reversed by the squaramide containing same chiral source as catalyst. DFT calculations revealed origin observed stereochemistry reversal enantioselectivity.

Язык: Английский

Процитировано

42

Ag-Catalyzed Asymmetric Interrupted Barton–Zard Reaction Enabling the Enantioselective Dearomatization of 2- and 3-Nitroindoles DOI
Wei‐Cheng Yuan, Xinmeng Chen, Jian‐Qiang Zhao

и другие.

Organic Letters, Год журнала: 2022, Номер 24(3), С. 826 - 831

Опубликована: Янв. 14, 2022

We disclose a Ag-catalyzed asymmetric interrupted Barton–Zard reaction of α-aryl-substituted isocyanoacetates with 2- and 3-nitroindoles, which enables the dearomatization nitroindoles hence offers rapid access to an array optically active tetrahydropyrrolo[3,4-b]indole derivatives bearing three contiguous stereogenic centers, including two tetrasubstituted chiral carbon atoms pretty outcomes (up 99% yield, 91:9 dr, 96% ee). The synthetic potential protocol was showcased by gram-scale versatile transformations product.

Язык: Английский

Процитировано

35

Recent Dearomatization Strategies of Benzofurans and Benzothiophenes DOI

Sindoori R. Nair,

Beeraiah Baire

Asian Journal of Organic Chemistry, Год журнала: 2021, Номер 10(5), С. 932 - 948

Опубликована: Март 10, 2021

Abstract This review article discusses about the recent developments in area of strategies for dearomatization benzofurans and benzothiophenes (2010–2020). The readers can understand current state art this intriguingly important organic synthesis generation diversely functionalized molecules, polycyclic systems from highly abundant benzothiophenes. We hope that would help synthetic community design development new as well further growth novel rapidly growing research.

Язык: Английский

Процитировано

35

Dearomatization of 3-Nitroindoles Enabled Using Palladium-Catalyzed Decarboxylative [4 + 2] Cycloaddition of 2-Alkylidenetrimethylene Carbonates DOI

Pei‐Hao Dou,

Shu‐Pei Yuan,

Yan Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(9), С. 6025 - 6037

Опубликована: Апрель 18, 2022

A dearomatization process of 3-nitroindoles enabled using palladium-catalyzed decarboxylative [4 + 2] cycloaddition either 2-alkylidenetrimethylene carbonates or 2-(hydroxymethyl)-3-arylallyl has been developed, affording a wide range indoline-fused tetrahydropyrans in good yields with excellent diastereoselectivities. This reaction features substrate scope and mild conditions represents the first example application π-allyl palladium 1,4-[O,C]-dipole species for dearomative electron-deficient heteroarenes.

Язык: Английский

Процитировано

27

Photoredox-Catalyzed Intermolecular Hydroalkylative Dearomatization of Electron-Deficient Indole Derivatives DOI

Xu‐Lun Huang,

Yuan‐Zheng Cheng,

Xiǎo Zhang

и другие.

Organic Letters, Год журнала: 2020, Номер 22(24), С. 9699 - 9705

Опубликована: Дек. 9, 2020

Dearomatization of indole derivatives offers a straightforward approach to access diverse indolines. To date, the corresponding dearomative transformations involving electron-deficient indoles are limited. Herein, we report one-electron strategy for dearomatization via photoredox-catalyzed hydroalkylation employing commercially available glycine as hydrofunctionalization reagents. Followed by DBU-mediated lactamization, structurally appealing lactam-fused indolines obtained in good excellent yields with exclusive selectivity.

Язык: Английский

Процитировано

38

Catalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5H-thiazol-4-ones: stereoselective construction of dihydrobenzofuran-bridged polycyclic skeletons DOI
Jian‐Qiang Zhao, Zhou Shun, Zhen‐Hua Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(22), С. 6330 - 6336

Опубликована: Янв. 1, 2021

An organocatalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5 H -thiazol-4-ones is developed for the construction dihydrobenzofuran-bridged polycyclic skeletons with good results.

Язык: Английский

Процитировано

30

Dearomatization of 3‐Nitroindoles with Highly γ‐Functionalized Allenoates in Formal (3+2) Cycloadditions DOI

Léo Birbaum,

Laurent Gillard,

Hélène Gérard

и другие.

Chemistry - A European Journal, Год журнала: 2019, Номер 25(60), С. 13688 - 13693

Опубликована: Сен. 11, 2019

3-Nitroindoles are easily reacted with highly substituted γ-allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids combined for first time 3-nitroindole. The corresponding dearomatized (3+2) tricyclic cycloadducts obtained α-regioisomers exclusively. DFT computations shed light on this multi-step reaction mechanism selectivities observed sequence.

Язык: Английский

Процитировано

31