Two photons are better than one: continuous flow synthesis of ꞵ-lactones through a doubly photochemically-activated Paternò-Büchi reaction DOI Creative Commons
Federica Minuto, Emanuele Farinini, Serena De Negri

et al.

Journal of Flow Chemistry, Journal Year: 2023, Volume and Issue: 14(1), P. 149 - 159

Published: Dec. 15, 2023

Abstract In this paper we report a [2 + 2] cycloaddition reaction between ketenes and benzils, characterized by an unusual double photochemical activation triggered visible light. Employment of flow system optimization conditions through Design Experiments resulted in moderate to good yields the corresponding β-lactones. A thorough computational analysis allowed elucidate mechanism justify observed diastereoselectivity. The was also successfully tested with mixed showing complete regioselectivity. Graphical abstract

Language: Английский

Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

13

Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks DOI
Ke Xu, Heping Li,

Yan‐Ling Ji

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1006 - 1011

Published: Jan. 16, 2025

Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to diverse and functionalized array of cyclobutene frameworks adorned with quaternary carbon center. This approach broadens the repertoire 2-alkynylnaphthols alkenes, offering versatile platform for construction complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates wide substrate scope an impressive functional group tolerance, yielding products high efficiency, up 97% yield, excellent enantiomeric excess 97%. simplicity scaling this process, coupled ease converting these into variety substituted products, significantly enhances utility method.

Language: Английский

Citations

1

Visible-light-mediated substituent-controlled regiodivergent (2 + 2)/(3 + 2) cycloadditions for the synthesis of aza-analogs of β-lactam and γ-fused lactam derivatives DOI

Wei‐Fang Zuo,

Yang Zhang,

Yulin Luo

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(13), P. 3576 - 3582

Published: Jan. 1, 2024

Substituent-controlled regiodivergent synthesis of aza-analogs β-lactam and γ-fused lactam derivatives via the visible-light-induced Wolff rearrangement α-diazoketones azo esters.

Language: Английский

Citations

5

Metal-free assembly of diverse polysubstituted pyridines via an efficient cascade approach using tertiary enaminones and α,β-unsaturated sulfonylketimines DOI
Xiang Li, Qiwen Pang, Yang Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2607 - 2612

Published: Jan. 1, 2024

A metal-free, scalable, and cascade protocol for assembling diverse polysubstituted pyridines from tertiary enaminones α,β-unsaturated sulfonylketimines by cleaving C–N/N–S bonds is reported.

Language: Английский

Citations

4

Senior Undergraduate Organic Chemistry Lab Course: Light-Driven Scaffold Editing DOI
Qian‐Qian Yang, Jiaxin Li, Gu Zhan

et al.

Journal of Chemical Education, Journal Year: 2025, Volume and Issue: unknown

Published: May 6, 2025

Language: Английский

Citations

0

Photochemically Induced Approaches to the Syntheses of β‐Lactams DOI
Vijay Kumar Das, Imtiaz Ahmed, Nikita Gupta

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(22), P. 4548 - 4558

Published: Oct. 8, 2024

Abstract The synthesis of β‐lactam scaffolds is paramount importance due to their extensive applications in pharmaceuticals, particularly as antibiotics. Visible light photocatalysis has emerged a revolutionary approach this domain, providing sustainable and efficient pathway for construction. In review, we meticulously discuss the recent developments photocatalysed frameworks. A key focus Staudinger reaction, traditionally cornerstone synthesis, its adaptation visible photocatalysis. We explore mechanistic intricacies reaction under photochemical conditions, along with other pivotal cyclization strategies enabled by light. By illuminating novel photocatalytic routes β‐lactams, review provides thorough understanding state‐of‐the‐art techniques sets stage future innovations green these critical compounds.

Language: Английский

Citations

1

Synthesis of α-Chiral Amides via Synergistic Visible-light-induced Wolff Rearrangement and Asymmetric NHC Catalysis DOI

Jiaomei Wang,

Yangxu Chen,

Siyan Miao

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(35), P. 15287 - 15291

Published: Jan. 1, 2024

Herein, a visible-light-induced chiral N-heterocyclic carbene (NHC) catalyzed asymmetric amination of ketenes has been developed. This strategy provides facile synthetic protocol for the efficient construction α-chiral amides.

Language: Английский

Citations

0

The Wolff Rearrangement DOI

João P. Castro,

Nuno R. Candeias

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Language: Английский

Citations

0

Two photons are better than one: continuous flow synthesis of ꞵ-lactones through a doubly photochemically-activated Paternò-Büchi reaction DOI Creative Commons
Federica Minuto, Emanuele Farinini, Serena De Negri

et al.

Journal of Flow Chemistry, Journal Year: 2023, Volume and Issue: 14(1), P. 149 - 159

Published: Dec. 15, 2023

Abstract In this paper we report a [2 + 2] cycloaddition reaction between ketenes and benzils, characterized by an unusual double photochemical activation triggered visible light. Employment of flow system optimization conditions through Design Experiments resulted in moderate to good yields the corresponding β-lactones. A thorough computational analysis allowed elucidate mechanism justify observed diastereoselectivity. The was also successfully tested with mixed showing complete regioselectivity. Graphical abstract

Language: Английский

Citations

0