Photoreductive Alkylative Dearomatization of N‐Alkyl Pyridin‐1‐ium Salts: Site Selective Access to 4‐Alkyl 1,4‐Dihydropyridines DOI

Chong‐Hui Xu,

Liang Zeng,

Ming Hu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(3)

Published: Nov. 28, 2023

Abstract A visible light photoreductive dearomatizative alkylation of N ‐alkyl pyridinium salts for producing 4‐alkyl‐1,4‐dihydropyridines is described. The reaction harnesses both as the alkyl radical precursors to initiate and 1,4‐dihydropyridin‐4‐yl‐based alkylating reagents terminate reaction. In contrast reported electroreductive procedure via key dihydropyridine intermediates, mechanistic studies demonstrate that this proceeds directly addition across ring followed by single electron oxidant (SEO) dearomatization.

Language: Английский

Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol DOI
Yue Jia, Zhihan Zhang,

Guoming Yu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(51)

Published: Nov. 8, 2023

The exploration of value-added conversions naturally abundant amino acids has received considerable attention from the synthetic community. Compared with well-established asymmetric decarboxylative transformation, deaminative transformation still remains a formidable challenge, mainly due to lack effective strategies for C-N bond activation and potential incompatibility chiral catalysts. Here, we disclose photoinduced Cu-catalyzed coupling reaction arylboronic acids. This new protocol provides series significant phenylacetamides in generally good yields excellent stereoselectivity under mild green conditions (42-85 % yields, up 97 ee). Experimental investigations theoretical calculations were performed reveal crucial role additional phenols improving catalytic efficiency enantiocontrol.

Language: Английский

Citations

15
Advancements in organocatalysis for radical-mediated asymmetric synthesis: A recent perspective DOI
Fuxing Yang, Tao Huang, Yu‐Mei Lin

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 4(4), P. 100812 - 100812

Published: Nov. 20, 2023

Language: Английский

Citations

8
Nucleophilicity of 4‐(Alkylthio)‐3‐imidazoline Derived Enamines DOI Creative Commons

Magenta J. Hensinger,

Andreas Eitzinger, Oliver Trapp

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(2)

Published: Oct. 18, 2023

Imidazolidine-4-thiones (ITOs) are cyclic, secondary amines that were considered as potential prebiotic organocatalysts for light-driven α-alkylations of aldehydes by bromoacetonitrile (BAN). Recent studies showed the initially supplied ITOs represent pre-catalyst because they undergo S-alkylation with BAN to give 4-(alkylthio)-3-imidazolines (TIMs). Given same reagent mix undergoes is also effective in dark, we synthesized ten ITO- or TIM-derived enamines and characterized their nucleophilic reactivities kinetic acetonitrile. The experimental second-order rate constants k

Language: Английский

Citations

5
Visible-Light-Induced Photoredox 1,2-Dialkylation of Styrenes with α-Carbonyl Alkyl Bromides and Pyridin-1-ium Salts DOI

Chong‐Hui Xu,

Gui‐Fen Lv,

Jing‐Hao Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 281 - 290

Published: Dec. 18, 2023

A visible-light-driven photoredox dialkylation of styrenes with α-carbonyl alkyl bromides and pyridin-1-ium salts for the synthesis polysubstituted 1,4-dihydropyridines is reported. This reaction enables formation two new C(sp3)–C(sp3) bonds in a single step provides strategy that employs as functionalized alkylating reagents via dearomatization to directly trap resulting radicals from radical addition alkenes then terminate alkene dialkylation.

Language: Английский

Citations

5
Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond DOI Open Access

Jiaxia Pu,

Xiaoying Jia,

Lirong Han

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(8), P. 2591 - 2591

Published: Jan. 1, 2023

In recent years, the photochemical organic transformation promoted by visible light has aroused interest of chemists.Compared with traditional methods, photoredox catalysis using as renewable energy been proved to be a mild and powerful tool, which can promote activation molecules single electron transfer (SET) process.There are lot amino functional groups in structures many natural products, also important structural units some drug materials.Therefore, activating C-N bond these substances carrying out coupling reactions C-C formation, structure compounds effectively modified, so obtain various functionalization.Therefore, this study become an research field synthesis.The results breaking its application formation reaction years reviewed, representative examples mechanisms discussed.

Language: Английский

Citations

4
Enterolignans: from natural origins to cardiometabolic significance, including chemistry, dietary sources, bioavailability, and activity DOI Creative Commons
Emily P. Laveriano-Santos, Carlos Luque‐Corredera, Marta Trius‐Soler

et al.

Critical Reviews in Food Science and Nutrition, Journal Year: 2024, Volume and Issue: unknown, P. 1 - 21

Published: July 1, 2024

The enterolignans, enterolactone and enterodiol, the main metabolites produced from plant lignans by gut microbiota, have enhanced bioavailability activity compared to their precursors, with beneficial effects on metabolic cardiovascular health. Although extensively studied, biosynthesis, cardiometabolic effects, other therapeutic implications of mammalian are still incompletely understood. aim this review is provide a comprehensive overview these phytoestrogen based up-to-date information reported in studies wide range disciplines. Established novel synthetic strategies described, as various lignan dietary sources, proposed pathway for conversion enterolignans. methodologies used enterolignan analysis available data pharmacokinetics summarized bioactivity explored detail. special focus given research health benefits microbial-derived underscores critical role lignan-rich diets promoting

Language: Английский

Citations

1
Synthesis and Functionalization of Natural Products with Light-Driven Reactions DOI
Suman Majee, Km. Anjali, Satya P. Yadav

et al.

Published: Dec. 31, 2024

Language: Английский

Citations

1
Cr-mediated photocatalytic decarboxylative coupling of alpha-oxo acids with benzylic pyridinium salts DOI
Jia Cao, Yan Liu, Zhixiang Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3242 - 3249

Published: Jan. 1, 2024

We developed a method for chromium/photoredox dual catalytic synthesis of ketones using α-oxo acids with benzylic pyridinium salts.

Language: Английский

Citations

0
Visible Light Induced Copper‐Catalyzed Enantioselective Deaminative Arylation of Amino Acid Derivatives Assisted by Phenol DOI Open Access
Yue Jia, Zhihan Zhang,

Guoming Yu

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(51)

Published: Nov. 8, 2023

Abstract The exploration of value‐added conversions naturally abundant amino acids has received considerable attention from the synthetic community. Compared with well‐established asymmetric decarboxylative transformation, deaminative transformation still remains a formidable challenge, mainly due to lack effective strategies for C−N bond activation and potential incompatibility chiral catalysts. Here, we disclose photoinduced Cu‐catalyzed coupling reaction arylboronic acids. This new protocol provides series significant phenylacetamides in generally good yields excellent stereoselectivity under mild green conditions (42–85 % yields, up 97 ee). Experimental investigations theoretical calculations were performed reveal crucial role additional phenols improving catalytic efficiency enantiocontrol.

Language: Английский

Citations

1
Photoreductive Alkylative Dearomatization of N‐Alkyl Pyridin‐1‐ium Salts: Site Selective Access to 4‐Alkyl 1,4‐Dihydropyridines DOI

Chong‐Hui Xu,

Liang Zeng,

Ming Hu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(3)

Published: Nov. 28, 2023

Abstract A visible light photoreductive dearomatizative alkylation of N ‐alkyl pyridinium salts for producing 4‐alkyl‐1,4‐dihydropyridines is described. The reaction harnesses both as the alkyl radical precursors to initiate and 1,4‐dihydropyridin‐4‐yl‐based alkylating reagents terminate reaction. In contrast reported electroreductive procedure via key dihydropyridine intermediates, mechanistic studies demonstrate that this proceeds directly addition across ring followed by single electron oxidant (SEO) dearomatization.

Language: Английский

Citations

1