Aromatic Amine Catalysts for the O2-Mediated Cross-Dehydrogenative Phenothiazination Reaction? DOI
Frédéric W. Patureau, Shiny Nandi, Alina Paffen

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(09), P. 967 - 972

Published: Dec. 11, 2023

Abstract Metal-free aromatic amines have been utilized recently as redox-active catalysts in various oxidative coupling reactions. In this study, we investigated a series of and their potential redox catalytic activity, particular compared to our previously reported amino-Te(II) catalysts. The O2-mediated cross-dehydrogenative phenothiazination phenols was benchmark test reaction, well the indoles. We thus identified proton sponge an effective amine catalyst. It moreover found that although displays clear it is generally less active than phenotellurazine insights provided by study should guide future research efforts for development innovative redox-catalyzed

Language: Английский

O2-Mediated Cu-Catalyzed Dehydrogenative Phenothiazination DOI

Fang Xiao,

Xingben Wang,

Ben Ebel

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 2, 2025

In contrast to what one can be led believe upon inspecting some of the recent literature, dehydrogenative phenothiazination reaction does not require onerous technologies, complicated setups, or advanced catalysts in order mild and sustainable. We demonstrate this herein with a most facile, cost-effective, sustainable Cu(II) catalyzed method, under 1 atm O2 at room temperature methanol, providing broad scope high yields. These new results further set among green practical coupling concepts chemistry.

Language: Английский

Citations

0
Impact of Adding N-hexylamine to Nickel Metallophotoredox C–N Coupling to Form Diarylamines DOI
Haiyang Wang, Fujun Li, Wenbo Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

The mechanistic understanding of how alkylamines impact Ni-metallophotoredox C–N coupling to form diarylamines remains unclear. In this study, 12-alkylamines were evaluated as additives determine their effects on the synthesis in a flow photochemical system. Notably, n-hexylamine demonstrated most significant promotional effect. Spectroscopic studies and experimental data reveal substitutes DABCO Ni catalyst ligand, enhancing yields particularly sterically hindered arylamines.

Language: Английский

Citations

0
Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis DOI Creative Commons

Ryota Tajima,

Keisuke Tanaka,

Kazuhiro Aida

et al.

Published: June 6, 2024

The bibenzyl skeleton is prevalent in numerous natural products and other biologically active compounds. Radical homocoupling provides a straightforward approach for synthesizing bibenzyls single step, with the reductive of benzyl halides undergoing extensive development. Unlike bromides tailored pre-cursors used visible light-mediated homocoupling, chlorides offer greater abundance chemical stabil-ity. Nevertheless, achieving chemoselective cleavage C–Cl bond poses significant challenges, only limited number studies reported to date. Herein, we demonstrate catalytic facilitated by zirconocene photoredox catalysis. This cooperative system promotes under mild conditions supports wide range chlorides, includ-ing those derived from pharmaceutical agents. Our preliminary mechanistic investigations highlight pivotal role hydrosilane cycle.

Language: Английский

Citations

2
Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis DOI Creative Commons

Ryota Tajima,

Keisuke Tanaka,

Kazuhiro Aida

et al.

Precision Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 7, 2024

The bibenzyl skeleton is prevalent in numerous natural products and other biologically active compounds. Radical homocoupling provides a straightforward approach for synthesizing bibenzyls single step with the reductive of benzyl halides undergoing extensive development. Unlike bromides tailored precursors used visible-light-mediated homocoupling, chlorides offer greater abundance chemical stability. Nevertheless, achieving chemoselective cleavage C-Cl bond poses significant challenges, only limited number studies reported to date. Herein, we demonstrate catalytic facilitated by zirconocene photoredox catalysis. This cooperative system promotes under mild conditions supports wide range chlorides, including those derived from pharmaceutical agents. Our preliminary mechanistic investigations highlight pivotal role hydrosilane cycle.

Language: Английский

Citations

0
Electrochemical C–H/N–H Coupling of Phenothiazines with Halogenated Phenols DOI
A. Kononov, A. D. Zlygostev,

M. A. Khvorova

et al.

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(11), P. 3104 - 3112

Published: Nov. 1, 2024

Language: Английский

Citations

0
Aromatic Amine Catalysts for the O2-Mediated Cross-Dehydrogenative Phenothiazination Reaction? DOI
Frédéric W. Patureau, Shiny Nandi, Alina Paffen

et al.

Synlett, Journal Year: 2023, Volume and Issue: 35(09), P. 967 - 972

Published: Dec. 11, 2023

Abstract Metal-free aromatic amines have been utilized recently as redox-active catalysts in various oxidative coupling reactions. In this study, we investigated a series of and their potential redox catalytic activity, particular compared to our previously reported amino-Te(II) catalysts. The O2-mediated cross-dehydrogenative phenothiazination phenols was benchmark test reaction, well the indoles. We thus identified proton sponge an effective amine catalyst. It moreover found that although displays clear it is generally less active than phenotellurazine insights provided by study should guide future research efforts for development innovative redox-catalyzed

Language: Английский

Citations

1