Concise synthesis of 2,4-bis(fluoroalkyl)quinoline derivatives from arylamines DOI

Yafen He,

Wei Zhang, Jinbo Hu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134046 - 134046

Published: May 24, 2024

Language: Английский

Visible-Light-Induced Glycosylation/Annulation of 2-Isocyanobiaryls and Glycosyl NHP Esters to Access Nonclassical Heteroaryl C-Glycosides DOI

Guanghui Lv,

Yangyang Wang,

Penghua Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

A photoredox-promoted cascade glycosylation/cyclization reaction of 2-isocyanobiaryls and glycosyl NHP esters was established for the synthesis nonclassical heteroaryl C-glycosides. This methodology is characterized by an exceedingly simple system, high diastereoselectivity, good functional group tolerance. In contrast to traditional strategies, this innovative approach circumvents need temperature, transition metal, photocatalyst, offering environmentally friendly efficient protocol.

Language: Английский

Citations

0
NHC-Catalyzed Tandem Reaction: A Strategy for the Synthesis of 2-Pyrrolidinone-Functionalized Phenanthridines DOI
Nengneng Zhou, Lei Wang,

Fangli Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16556 - 16565

Published: Nov. 16, 2023

Herein, an N-heterocyclic carbene (NHC)-catalyzed tandem cyclization/addition/cyclization reaction of 2-isocyanobiaryls and α-bromo-N-cinnamylamides for the synthesis 2-pyrrolidinone-functionalized phenanthridines is developed. This protocol features a radical cascade process, broad substrate scope, good functional group compatibility under metal- oxidant-free conditions.

Language: Английский

Citations

4
Visible-Light-Mediated Annulation/Thiolation of 2-Isocyanobiaryls with Disulfides to Organoylthiophenanthridines Derivatives DOI
Hongyu Wu, Zhong Cao, Shiqi Li

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17322 - 17329

Published: Dec. 4, 2023

A visible-light-induced annulation/thiolation of 2-isocyanobiaryls with dialkyl(aryl)disulfides has been established, delivering a sustainable and atom-economic route to 6-organoylthiophenanthridines wild functional group tolerance good excellent yields under oxidant-, base-, transition-metal-free conditions.

Language: Английский

Citations

4
Electro‐oxidative Methylation of 2‐Isocyanobiaryls Using N,N‐dimethylformamide (DMF) as Carbon Source: Synthesis of 6‐Methylphenanthridines DOI

Kannika La‐ongthong,

Teera Chantarojsiri, Darunee Soorukram

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(9)

Published: March 16, 2024

A benign electrochemical method to access 6-methylphenanthridines from 2-isocyanobiaryls using N,N-dimethylformamide (DMF) as a methyl source is reported. The protocol operates at ambient temperature without the need for harmful methylating reagents. Mechanistic studies suggested that DMF delivered methylene synthon, followed by reduction cathode and tautomerization. offers environmental benefits avoiding metal-based reagents harsh conditions.

Language: Английский

Citations

1
Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations DOI
G. K. Surya Prakash, Alexander Knieb

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 5, 2024

Abstract Fluoroalkylation serves as a pivotal strategy for chemists to precisely alter the properties of small molecules. Among established fluoroalkylation protocols, sulfone and sulfinate reagents stand out versatile tools these reactions, particularly in mono-, di-, trifluoromethylations. Their versatility lies offering multiple pathways, encompassing electrophilic, nucleophilic, well radical mechanisms, thus providing diverse routes controlled molecular modifications through variety very exciting mechanistic paths. 1 Introduction 2 Monofluoromethylation Strategies 2.1 Fluorobis(phenylsulfonyl)methane (FBSM) 2.2 2-Fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide (FBDT) 2.3 Benzothiazole-SO2CH2F, NaSO2CH2F, ClSO2CH2F 2.4 PhSO2CH2F 3 Difluoromethylation 3.1 PhSO2CF2H 3.2 Benzothiazole-SO2CF2H 3.3 2-PyrSO2CF2H 3.4 NaSO2CF2H 4 Trifluoromethylation 4.1 PhSO2CF3 4.2 2-PyrSO2CF3 4.3 Benzothiazole-SO2CF3 4.4 NaSO2CF3 4.4.1 Electrochemical Approaches 4.4.2 Photochemical 4.4.3 Other Noteworthy 5 Conclusion

Language: Английский

Citations

1
Electrochemical trifluoroalkylation/annulation for the synthesis of CF3-functionalized tetrahydroquinolines and dihydroquinolinones DOI

Hao-Zeng Wu,

Zhong-Shan Teng,

Yu-Xin Ke

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(42), P. 8579 - 8583

Published: Jan. 1, 2023

Tuning the electronic structure of protecting groups on nitrogen atom substrates has emerged as an effective strategy to achieve tandem trifluoromethylation/C(sp2)-H annulation using Langlois' reagent CF3 source for electrochemical synthesis functionalized tetrahydroquinolines and dihydroquinolinones.

Language: Английский

Citations

2
Photoredox-catalyzed addition of isocyanides with boracene-based alkylborate: Construction of 6-alkylphenanthridine DOI

Li Liu,

Xingkang Yu,

Wenyan Zhao

et al.

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 134, P. 154881 - 154881

Published: Dec. 9, 2023

Language: Английский

Citations

2
Concise Synthesis of 2,4-Bis(Fluoroalkyl)Quinoline Derivatives from Arylamines DOI

Yafen He,

Wei Zhang, Jinbo Hu

et al.

Published: Jan. 1, 2024

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Language: Английский

Citations

0
Concise synthesis of 2,4-bis(fluoroalkyl)quinoline derivatives from arylamines DOI

Yafen He,

Wei Zhang, Jinbo Hu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134046 - 134046

Published: May 24, 2024

Language: Английский

Citations

0