Photo‐catalyzed Stereospecific Synthesis of Trisubstituted Alkenes Incorporating 3,3‐Difluoro‐γ‐Lactams from Morita‐Baylis‐Hillman Acetates and N‐Allylbromodifluoroacetamides DOI Open Access
Xi Chen,

Chi Ai,

Yuting Wang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Abstract A photocatalytic methodology has been devised for the stereoselective construction of trisubstituted alkenes incorporating 3,3‐difluoro‐γ‐lactams in 17–93% yields via a radical cascade process utilizing MBH acetates and N ‐allylbromodifluoroacetamides as starting materials. The reaction mechanism involves single‐electron transfer, 5 ‐ exo trig cyclization, addition, elimination fashion.

Language: Английский

Photoredox-Catalyzed Redox-Neutral Decarboxylative C–H Acylations of Coumarins with α-Keto Acid DOI
Bin Sun, Yingying Wang, Jia‐Yin Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2466 - 2470

Published: March 31, 2023

A novel and green photocatalytic strategy for the synthesis of C-4-acylated coumarins with α-keto acids 3-nitrocoumarin has been developed. This operationally simple protocol works under mild reaction conditions, providing convenient access to 4-acyl coumarin derivatives. The control experimental results showed that nitro radical produced by cleavage C-N bond acts as an electron acceptor complete cycle, achieving a redox-neutral reaction.

Language: Английский

Citations

11

Photoinduced tandem radical cyclization/heteroarylation of N-allylbromodifluoroacetamides with quinoxalin-2(1H)-ones or coumarins under metal- and photocatalyst-free conditions DOI
Wei Zhao,

Liangming Xuan,

Yang Liu

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(22), P. 10744 - 10750

Published: Jan. 1, 2023

A photocatalyst-free visible-light-promoted tandem intramolecular cyclization/heteroarylation between bromodifluoroacetamides and quinoxalin-2(1 H )-ones or coumarins was developed. The process could generate a broad range of α , -difluoro-γ-lactams.

Language: Английский

Citations

9

Recent Progress in Visible Light‐Mediated Synthesis of γ‐lactams DOI Open Access
Suman Pradhan, Shoubhik Das

Helvetica Chimica Acta, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

Abstract The integration of sustainable practices, such as employing renewable light sources for synthesizing valuable synthetic scaffolds, has been progressing over the past few decades. Among these noteworthy organic frameworks, lactams, particularly γ‐lactams, have established their prominence due to extensive applications in pharmaceutical, agricultural, and medicinal domains. This growing significance γ‐lactams spurred considerable interest synthesis, especially via milder, more sustainable, environmentally friendly methods. In recent years, numerous innovative reaction mechanisms explored, highlighting how photocatalysis can enable formation from readily accessible precursors through C−N bond cyclization processes. review emphasizes potential photocatalytic strategies not only enhance current methods but also foster development greener chemical processes future.

Language: Английский

Citations

0

Nickel-Catalyzed Aminofluoroalkylative Cyclization of Styrenes with Ethyl Fluoroacetate and Anilines toward Fluoro-γ-Lactams DOI
Fengxiang Zhu, Ziyan Li, Xiao‐Feng Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8535 - 8539

Published: Nov. 20, 2023

A novel method for the nickel-catalyzed multicomponent aminofluoroalkylation/cyclization of styrenes with ethyl fluoroacetate and anilines has been developed. This protocol provides general efficient access to a diverse range fluoro-γ-lactams from simple readily available starting materials. Control experiments prove involvement radical intermediates excluded presence 2-fluoro-N-phenylacetamide.

Language: Английский

Citations

8

Photocatalysis as a green alternative toolkit for the construction of nitrogen-enriched heterocycles via the direct and indirect activation of alkynes/alkenes DOI
Anupam Das, Siddan Gouthaman, K. R. Justin Thomas

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 26(3), P. 1223 - 1280

Published: Dec. 18, 2023

By harnessing the reactivity of alkynes and alkenes under photochemical conditions, novel pathways have been unlocked to construct N -heterocyclic compounds, allowing for more efficient sustainable synthesis.

Language: Английский

Citations

6

Photoredox-Catalyzed Synthesis of 3,3-Difluoro-γ-lactams via 1,5-Hydrogen Atom Transfer-Involved Alkyne Difunctionalization and C–N Cleavage DOI
Lin Tang,

Fengjuan Jia,

Ge Lv

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9903 - 9908

Published: Nov. 8, 2024

This manuscript describes the application of a 1,5-hydrogen atom transfer strategy in photoredox-catalyzed hydrodifluoroalkylation alkynes. The approach utilizes sequential cascade process difluoroalkylation, transfer, C(sp

Language: Английский

Citations

2

Visible‐Light‐Driven Sulfonamidation of Arylazo Sulfonesthrough One‐Pot Multicomponent Reaction DOI
Truong Giang Luu, Hee‐Kwon Kim

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(8)

Published: July 8, 2023

Abstract Sulfonamide is one of the most important structures in organic chemistry due to its frequent appearance natural products as well pharmaceuticals. This study reports a visible‐light‐promoted strategy for synthesis sulfonamides from arylazo sulfones. One‐pot tri‐component reactions were conducted using sulfones, DABSO, and amines presence CuBr 2 coupling catalyst under irradiation with blue LEDs prepare various good yields mild conditions. method could be used effectively produce variety useful sulfonamides.

Language: Английский

Citations

5

Electroreductive Umpolung Enabling Reformatsky‐Type Reaction of Bromodifluoroamides with Aldehydes/Ketones DOI
Zhengjia Shen, Jia‐Lin Tu, Lin Guo

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4507 - 4512

Published: Nov. 3, 2023

Abstract An electrochemical Reformatsky‐type reaction of bromodifluoroamides with aldehydes/ketones via electron reductive umpolung is reported, leading to the generation a series β‐hydroxy‐α,α‐difluoro amides in moderate good yields. This protocol tolerated variety commercially available alkyl ketone, and aromatic aldehydes, featuring broad substrate scope functional group tolerance under transition metal‐free conditions without metal reduction reagents. Control experiment indicated that proceeded an pathway.

Language: Английский

Citations

5

Cu-catalyzed three-component aminodifluoroalkylative cyclization of styrenes: Access to α,α-difluoro-γ-lactams DOI
Fengxiang Zhu, Jiajia Luo, Pengbo Zhang

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 556, P. 113899 - 113899

Published: Feb. 6, 2024

Language: Английский

Citations

0

Visible-light-induced photocatalytic four-component fluoroalkylation–dithiocarbamylation via difunctionalization of styrenes DOI
Patamawadee Silalai, Rungnapha Saeeng

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(42), P. 8437 - 8452

Published: Jan. 1, 2024

Herein we demonstrate that a visible-light-induced photocatalytic four-component fluoroalkylation-dithiocarbamylation is unified method for the fluoroalkylation of diverse activated fluoroalkyl halides, including monofluoroalkyl bromides, difluoroalkyl trifluoromethyl iodide, and perfluoroalkyl iodides. The synthetic value this has been demonstrated by transformations various substrates containing drug/natural product skeletons, gram scale reactions, further derivatizations fluorodithiocarbamate products. This work features an atom economical protocol simple to operate, does not require any additives or strong bases, can be carried out under mild conditions.

Language: Английский

Citations

0