Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes DOI Creative Commons
Michael Jakob, Luca Steiner,

Marius Göbel

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 17642 - 17653

Published: Nov. 15, 2024

The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare handle compounds, alkyl silanes are attractive substrates chemistry desilylative mesolysis the corresponding cations known be rapid. Here, we report successful application benzyl silane derivatives source radicals in dual NHC/photoredox-catalyzed radical–radical coupling acyl fluorides. Relatively electron-rich reacted smoothly afford ketones generally good yields, while optimization NHC photocatalyst allowed a wider scope including primary substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O- S-heteroatoms can also serve sources these

Language: Английский

Radical Reactions with N-Heterocyclic Carbene (NHC)-Derived Acyl Azoliums for Access to Multifunctionalized Ketones DOI

Hui Cai,

Xiaoqun Yang,

Shi‐Chao Ren

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(11), P. 8270 - 8293

Published: May 13, 2024

As one of the most important key intermediates, NHC-bound acylazolium-based ionic transformations have been intensively explored in past two decades. With expeditious development NHC-catalyzed radical recent years, acylazolium chemistry has reached another level, with number relevant publications increasing significantly. However, a summary focused on acylations NHC-derived acyl azoliums classified according to mechanistic difference not reported. Such detailed classification and deep analysis provide opportunities for better understanding history trend this field. In review, reactions N-heterocyclic carbene (NHC)-derived are systematically introduced. The achievements challenges within area also summarized discussed at end.

Language: Английский

Citations

24
NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes DOI
Zhaoyang Zhang, Jiayi Yang,

Shihao Li

et al.

Organic Chemistry Frontiers, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A strategy to obtain 1,2-alkenyl ketone products by radical relay coupling is proposed.

Language: Английский

Citations

0
Recent Advances in Strategies for Halide Atom Transfer (XAT) and Their Applications DOI

Yifeng Jiang,

Yanli Yin, Zhiyong Jiang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1733 - 1733

Published: Jan. 1, 2024

Language: Английский

Citations

3
1,2-Amidoarylcarbonylation of Styrenes to Access β-Acylamino Ketones by NHC-Catalyzed Radical Relay DOI
Dengyu Yin,

Lishuai Lu,

Ying Jiang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13085 - 13092

Published: Aug. 28, 2024

An amidoarylcarbonylation reaction of aromatic aldehydes and olefins with Katritzky pyridinium salts by N-heterocyclic carbene (NHC)-catalyzed radical relay to construct C-C C-N bonds good functional group tolerance is developed for the synthesis β-acylamino ketones. This gentle efficient approach offers a valuable style Mechanistic studies revealed that addition/coupling/elimination cascade process was involved in this reaction.

Language: Английский

Citations

2
Iron-Catalyzed Perfluoroalkylarylation of Styrenes with Arenes and Alkyl Iodides Enabled by Halogen Atom Transfer DOI

Hanqing Zhao,

Wanting Li,

Yong Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 18, 2024

A new iron-catalyzed three-component perfluoroalkylarylation of styrenes with alkyl halides and arenes has been established. Alkyl undergo halogen atom transfer methyl radicals to form in reactions initiated by a combination

Language: Английский

Citations

1
Dual N-Heterocyclic Carbene/Photoredox-Catalyzed Coupling of Acyl Fluorides and Alkyl Silanes DOI Creative Commons
Michael Jakob, Luca Steiner,

Marius Göbel

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 17642 - 17653

Published: Nov. 15, 2024

The combination of N-heterocyclic carbene (NHC) organocatalysis with photochemical activation is becoming increasingly established as an approach for conducting radical organic reactions under mild and practical conditions. As comparatively easy to prepare handle compounds, alkyl silanes are attractive substrates chemistry desilylative mesolysis the corresponding cations known be rapid. Here, we report successful application benzyl silane derivatives source radicals in dual NHC/photoredox-catalyzed radical–radical coupling acyl fluorides. Relatively electron-rich reacted smoothly afford ketones generally good yields, while optimization NHC photocatalyst allowed a wider scope including primary substrates. Furthermore, initial experiments revealed that organosilanes bearing N-, O- S-heteroatoms can also serve sources these

Language: Английский

Citations

0