Five-Membered Ring Systems: Furans and Benzofurans DOI

Halina Kwiecień,

Alicja Wodnicka

Progress in heterocyclic chemistry, Год журнала: 2019, Номер unknown, С. 281 - 323

Опубликована: Окт. 13, 2019

Язык: Английский

Phosphorus-Based Catalysis DOI Creative Commons
Changmin Xie, Andrew J. Smaligo,

Xian-Rong Song

и другие.

ACS Central Science, Год журнала: 2021, Номер 7(4), С. 536 - 558

Опубликована: Март 16, 2021

Phosphorus-based organocatalysis encompasses several subfields that have undergone rapid growth in recent years. This Outlook gives an overview of its various aspects. In particular, we highlight key advances three topics: nucleophilic phosphine catalysis, organophosphorus catalysis to bypass oxide waste, and compound-mediated single electron transfer processes. We briefly summarize five additional chiral phosphoric acid Lewis base iminophosphorane super phosphonium salt phase frustrated pair catalysis. Although it is not catalytic nature, also discuss novel discoveries are emerging phosphorus(V) ligand coupling. conclude with some ideas about the future

Язык: Английский

Процитировано

243

Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans DOI
Zhen Wang, Dong‐Chao Wang, Ming‐Sheng Xie

и другие.

Organic Letters, Год журнала: 2019, Номер 22(1), С. 164 - 167

Опубликована: Дек. 23, 2019

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asymmetric dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence a chiral copper complex, derived from Cu(OAc)2 and diphosphine ligand, series derivatives were obtained in high yields (75–91%) excellent enantioselectivities (90–98%). The utility this method showcased by facile transformation product.

Язык: Английский

Процитировано

55

Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita–Baylis–Hillman carbonates DOI

Xin-He Yang,

Jianping Li, Dong‐Chao Wang

и другие.

Chemical Communications, Год журнала: 2019, Номер 55(62), С. 9144 - 9147

Опубликована: Янв. 1, 2019

The phosphine-catalyzed asymmetric dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman (MBH) carbonates or allenoate was developed. reaction MBH resulted in a series cyclopentabenzofurans containing three contiguous stereocenters good to high yields, diastereoselectivities and enantioselectivities. use also gave the target product moderate enantioselectivity.

Язык: Английский

Процитировано

53

Organocatalytic Asymmetric Dearomatization of 3-Nitroindoles and 3-Nitrobenzothiophenes via Thiol-Triggered Diastereo- and Enantioselective Double Michael Addition Reaction DOI
Xinmeng Chen, Chuan-Wen Lei,

Deng‐Feng Yue

и другие.

Organic Letters, Год журнала: 2019, Номер 21(14), С. 5452 - 5456

Опубликована: Июнь 28, 2019

Organocatalytic asymmetric dearomatization of 3-nitroindoles and 3-nitrobenzothiophenes by reaction with ethyl 4-mercapto-2-butenoate has been developed. A range chiral tetrahydrothiopheneindolines tetrahydrothiophenebenzothiophenes bearing three contiguous stereocenters are obtained in high yields good diastereoselectivities excellent enantioselectivities. This is the first example thiol-triggered catalytic 3-nitrobenzothiophenes.

Язык: Английский

Процитировано

48

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

36

Recent Advances in Synthetic Strategies to 2,3-Dihydrobenzofurans DOI

Paolo Lupattelli,

Teresa Laurita, Rosarita D’Orsi

и другие.

Synthesis, Год журнала: 2020, Номер 52(10), С. 1451 - 1477

Опубликована: Март 16, 2020

This review gives an overview on recent developments in methods for the construction of compounds with 2,3-dihydrobenzo­furan core period 2012 to 2019. Interest 2,3-dihydrobenzofurans is constantly increasing. The are divided into intermolecular and intramolecular approaches. Intermolecular approaches subdivided according parent intermediate key reaction, while by which bond formed reaction. transformation benzofurans dihydrobenzofurans other miscellaneous also discussed. Approaches useful synthesis natural products emphasized. 1 Introduction 2 2.1 o-Quinone Methides o-Quinones 2.2 p-Quinone p-Quinones 2.3 Nitrogen-Containing Phenols Quinones 2.4 o-Hydroxyphenylcarbonyl Derivatives 2.5 Miscellaneous 3 Intramolecular 3.1 O–C2 Bond Forming 3.2 C2–C3 3.3 C3–Aryl 3.4 O–Aryl 4 From BF DHB 5 Rearrangements Aromatizations

Язык: Английский

Процитировано

35

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

Allenoates in organic synthesis DOI
Rahimeh Hajinasiri

Tetrahedron, Год журнала: 2022, Номер 126, С. 133053 - 133053

Опубликована: Окт. 5, 2022

Язык: Английский

Процитировано

18

Dearomatization of Nitro(hetero)arenes through Annulation DOI
Ning Wang, Jing Ren, Kaizhi Li

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(18)

Опубликована: Апрель 5, 2022

Abstract Dearomatization reactions employing simple aromatic compounds have showcased remarkable progress in the recent decade and emerged as one of most straightforward powerful tools for creation highly functionalized, three‐dimensional molecular frameworks commonly encountered medicinal chemistry life sciences. Among use, nitro(hetero)arenes, which feature a less pronounced character due to presence electron‐withdrawing nitro group, been extensively used different types dearomatization reactions. The dearomative annulation reaction serves versatile method construction complex polycyclic systems. This overview presents brief summary impressive advances nitro(hetero)arenes provides some inspirations future research.

Язык: Английский

Процитировано

17

Synthesis of Benzothienobenzofurans via Annulation of Electrophilic Benzothiophenes with Phenols DOI

Akhil Krishnan R,

Sheba Ann Babu,

P. R. Nitha

и другие.

Organic Letters, Год журнала: 2021, Номер 23(5), С. 1814 - 1819

Опубликована: Фев. 16, 2021

We have developed a metal-free, mild, and green synthetic route toward benzothieno[3,2-b]benzofurans by the annulation of 3-nitrobenzothiophene with phenols. The reaction was found to be general range substituted In addition, we could extend methodology for synthesis pentacenes demonstrate in gram-scale. Moreover, extended strategy benzothieno[2,3-b]benzofurans starting from 2-nitrobenzothiophenes.

Язык: Английский

Процитировано

22