Regioselective Alkylacylation of 1,3-Dienes by Merging N-Heterocyclic Carbene Catalysis with Photoinduced Palladium Catalysis DOI
Ying Huang,

You-Feng Han,

Chun-Lin Zhang

et al.

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

Published: Dec. 17, 2024

Herein, we develop a dual catalytic platform for the 1,2- or 1,4-alkylacylation reaction of 1,3-dienes with readily available alkyl halides and aldehydes by merging N-heterocyclic carbene catalysis photoinduced palladium catalysis. A series β,γ-unsaturated ketones are obtained in good to high yields. Mechanistic studies suggest that this involves radical process. The direct synthesis flavanone from salicylaldehyde exemplified potential capability platform.

Language: Английский

Homologation of Ketones: Direct Transformation of Alkyl Ketones to Aryl Ketones via Photoredox Catalyzed Deacylation-Aroylation Sequence DOI
Tian Wang, Zengyu Zhang, Fan Gao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6915 - 6920

Published: Aug. 8, 2024

Ketones, as essential functional group skeletons, have garnered significant interest due to their diverse transformations. Herein, we describe a versatile photoredox catalyzed deacylation-aroylation strategy that enables the direct transformation of alkyl ketones aryl ketones. This process involves deacylation dihydroquinazolinones derived from generate radicals, followed by subsequent NHC-catalyzed or NHC-mediated radical aroylation.

Language: Английский

Citations

9
Switching Mesoionic Carbene-Organocatalysis from Radical to Ionic Pathway through Base-Controlled Formation of Breslow Intermediates versus Breslow Enolates DOI Creative Commons
J. B. Jiao, Zengyu Zhang,

Guangyin Lu

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

N-heterocyclic carbene (NHC) organocatalysis has experienced significant advancements. Two distinct reaction pathways have been developed, ionic and radical, through Breslow intermediates (BIs) enolates (BI-s), respectively. The ability to selectively generate these is crucial for optimizing outcomes. In this paper we show that with mesoionic carbenes (MICs) it possible control the formation of BIs versus BI-s, use weak bases strong bases, Of particular interest coupling aldehydes alkyl halides yield ketones via an pathway.

Language: Английский

Citations

0
Recent Update on Catalytic Activity of N-Heterocyclic Carbene Supported on Graphene Nanosheets: A Mini Review DOI

Raed Muslim Mhaibes,

Abdul Amir H. Kadhum, H Al-Salman

et al.

Journal of Organometallic Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 123660 - 123660

Published: April 1, 2025

Language: Английский

Citations

0
Redox-Paired Reductive Heck Reaction and Oxidative Esterification Catalyzed by Mesoionic Carbenes DOI

B. HUANG,

Zengyu Zhang, J. B. Jiao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7419 - 7424

Published: Aug. 22, 2024

Paring a reductive reaction and an oxidative in one could be immensely important achieving atom economic environmental advantages. Herein, we report simple protocol that combines two such Heck reactions esterification by using mesoionic carbenes as catalysts to synthesize multiple valuable products under mild conditions.

Language: Английский

Citations

3
Boosting N-Heterocyclic Carbene Radical Organocatalysis with Nickel Chemistry: A Rational Mechanistic Study-Based Approach DOI
Ludivine Delfau,

Elena Mauro,

Jacques Pécaut

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(9), P. 7149 - 7156

Published: April 23, 2024

A cooperative NHC/nickel catalytic methodology has been developed for the synthesis of ketones employing aromatic aldehydes and tertiary alkyl iodides. All key steps postulated cycle were validated with comprehensive stoichiometric electrochemical studies, including reduction NiII by deprotonated Breslow intermediate, Ni0 promoted halogen-atom abstraction to generate transient radicals, coupling between latter persistent acyl thiazolium radical intermediate. Such a broadly proposed accepted, yet elusive, intermediate isolated studied single-crystal X-ray diffraction study.

Language: Английский

Citations

2
Cooperative Photoredox and N-Heterocyclic Carbene-Catalyzed Formal C-H Acylation of Cyclopropanes via Deconstruction-Reconstruction Strategy DOI Creative Commons
Fan Gao,

Tian Wang,

Xiaoyu Yan

et al.

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

Published: Jan. 1, 2024

Cooperative NHC/photoredox catalyzed deconstruction–reconstruction of aryl cyclopropanes was described to access various α-acylated cyclopropane derivatives.

Language: Английский

Citations

2
Regioselective Alkylacylation of 1,3-Dienes by Merging N-Heterocyclic Carbene Catalysis with Photoinduced Palladium Catalysis DOI
Ying Huang,

You-Feng Han,

Chun-Lin Zhang

et al.

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

Published: Dec. 17, 2024

Herein, we develop a dual catalytic platform for the 1,2- or 1,4-alkylacylation reaction of 1,3-dienes with readily available alkyl halides and aldehydes by merging N-heterocyclic carbene catalysis photoinduced palladium catalysis. A series β,γ-unsaturated ketones are obtained in good to high yields. Mechanistic studies suggest that this involves radical process. The direct synthesis flavanone from salicylaldehyde exemplified potential capability platform.

Language: Английский

Citations

1