Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI
Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Direct Synthesis of β-Amino Boronates via Amide α-C–H Bond Activation and C(sp3)–C(sp3) Coupling under Dual Ni/Photoredox Catalysis DOI

Zihao Hu,

Dong Wang, Tao Xu

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 547 - 553

Published: Dec. 26, 2023

Direct transformations of readily available amines or amides via C–H bond functionalization could provide a fast route for accessing complex molecules. While various groups have been successfully incorporated into the α position nitrogen atom with photoredox system activation, couplings functionalized alkyl halides are still very challenging. Herein, we report direct and convenient protocol β-amino boronates through C(sp3)–C(sp3) coupling α-bromoboronates. The mild conditions allow good functional group tolerance broad scope. application method in late-stage modification molecules further demonstrates its great potential organic synthesis. Mechanistic studies were also conducted, catalytic cycle is proposed.

Language: Английский

Citations

10

Visible Light-Mediated Monofluoromethylation/Acylation of Olefins by Dual Organo-Catalysis DOI Creative Commons

Jiuli Xia,

Yunliang Guo,

Zhiguang Lv

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 790 - 790

Published: Feb. 8, 2024

Monofluoromethyl (CH2F) motifs exhibit unique bioactivities and are considered privileged units in drug discovery. The radical monofluoromethylative difunctionalization of alkenes stands out as an appealing approach to access CH2F-containing compounds. However, this strategy remains largely underdeveloped, particularly under metal-free conditions. In study, we report on visible light-mediated three-component monofluoromethylation/acylation styrene derivatives employing NHC organic photocatalyst dual catalysis. A diverse array α-aryl-β-monofluoromethyl ketones was successfully synthesized with excellent functional group tolerance selectivity. mild CH2F generation from NaSO2CFH2 holds potential for further applications fluoroalkyl chemistry.

Language: Английский

Citations

3

Design of Dyes Based on the Quinoline or Quinoxaline Skeleton towards Visible Light Photoinitiators DOI Open Access
Ilona Pyszka, Beata Jędrzejewska

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(8), P. 4289 - 4289

Published: April 12, 2024

Dyes based on quinoline and quinoxaline skeletons were designed for application as visible light photoinitiators. The obtained compounds absorb electromagnetic radiation the border between ultraviolet light, which allows use of dental lamps sources during initiation photopolymerization reaction. Their another desirable feature is ability to create a long-lived excited state, enables chain reaction proceed through mechanism intermolecular electron transfer. In two-component photoinitiating systems, in presence an donor or hydrogen atom donor, synthesized show excellent abilities photoinitiate polymerization acrylates. control tests, efficiency using modified derivatives comparable that typical, commercial photoinitiator dentistry, camphorquinone. Moreover, tested requires small amount (only 0.04% by weight) initiate research also showed significant acceleration process shortening time. practice, this means new initiating systems can be used much lower concentrations without slowing down speed obtaining polymer materials. It worth emphasizing these two features system allow cost reduction reducing financial outlays both materials (photoinitiators) electricity.

Language: Английский

Citations

3

Dehydrogenative Coupling of Alkylamines with Primary Alcohols Forming α-Amino Ketones DOI
Tairin Kawasaki,

Tomohiro Tosaki,

S. Miki

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(26), P. 17566 - 17572

Published: June 17, 2024

Acceptorless dehydrogenative coupling reactions between C-H bonds offer straightforward and atom-economical methods connecting readily available materials while liberating gaseous hydrogen as the sole byproduct. Despite growing interest in such transformations, their realization still poses a significant challenge. Here we report photoinduced reaction of alkylamines with primary alcohols. adjacent to nitrogen oxygen are site-selectively cleaved, C-C bond is created carbon atoms cross-selective manner produce α-amino ketones. Diverse polar functionalities esters, amides, carboxylic acids survived, demonstrating broad applicability present method.

Language: Английский

Citations

3

Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis DOI
Lena Lezius,

Jannik Reimler,

Armido Studer

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 445 - 450

Published: Aug. 1, 2023

Abstract Cooperative NHC and photoredox catalysis has gained significant attention as an emerging research field in recent years. Herein, we report a cyclizing aminoacylation of alkenes, which is enabled through the combination these two catalytic modes. The key step radical/radical cross-coupling between persistent ketyl radical transient benzylic or aliphatic C-radical, generated cyclization oxidatively formed amidyl radical. Several carbamates, amides sulfonamides containing alkene moiety different acyl fluorides can be used substrates. resulting products are obtained moderate to good yields.

Language: Английский

Citations

8