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

Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis DOI Creative Commons
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize field from its beginnings up until mid-2023 and provide comprehensive coverage on synthetic methods current state mechanistic understanding. Chapters are split type bond formed, which include C(sp

Language: Английский

Citations

13
Stereoretentive Conversion to C-Glycosides from S-Glycosides via Ligand-Coupling on Sulfur(IV) DOI
Qian Yang,

Miaomiao Wen,

Yu-Jun Ruan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 954 - 960

Published: Jan. 21, 2025

A novel strategy is reported for the stereoselective synthesis of C(sp2)-C(sp3) C-glycosides, which converts heteroaryl S-glycosides into C-glycosides with retention configuration through a sequential process involving oxidation and Grignard reagent attack. The new method involves generation S(IV) intermediate, followed by ligand coupling glycosyl groups to yield C-glycosides. diverse were achieved good efficiency.

Language: Английский

Citations

1
Metal-free photoinduced denitrogenative alkylation of vinyl azides with alkyl radicals toward ketones DOI

Hui Yin,

Siqi Jian,

Xiujuan Feng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3124 - 3130

Published: Jan. 1, 2024

A metal-free method for the synthesis of ketones via a visible-light induced denitrogenative alkylation vinyl azides with alkyl radicals is presented.

Language: Английский

Citations

3
Photoredox/nickel dual-catalyzed deaminative cross-electrophile for allenylic alkylation with non-activated alkyl katritzky salts DOI
Zhao‐Zhao Zhou,

Xiaofeng Zhai,

Ke-Jian Xia

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5685 - 5694

Published: Jan. 1, 2024

The first allenylic alkylation with non-activated aliphatic amine derivatives, Katritzky salts, has been developed via photoredox/nickel dual-catalyzed reductive deaminative cross-electrophile coupling.

Language: Английский

Citations

2
Catalytic ring-strain release toward a facial and efficient synthesis of versatile C-glycosides DOI
Y. Zhang,

Xiao-Lin Zhang,

Han Ding

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110560 - 110560

Published: Oct. 1, 2024

Language: Английский

Citations

1
Concise synthesis of 3-C-glycosyl isocoumarins and 2- glycosyl-4H-chromen-4-ones DOI

Deng-Yin Liu,

Yu-Jun Ruan,

Xiaoli Wang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10390 - 10393

Published: Jan. 1, 2024

A new Ru-catalyzed C-H activation/cyclization reaction for the synthesis of 3-

Language: Английский

Citations

0
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