Recent Progress on NHC‐Catalyzed 1,6‐Conjugate Addition Reactions DOI
Jun Sun, Shichun Jiang,

Yonggui Liu

et al.

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 17, 2024

Abstract As a significant variant of the Michael reaction, 1,6‐addition reaction has undergone considerable development over past decade. This effective strategy enables synthesis variety novel and potentially bioactive functional molecules. In this review, we summarize recent progress in NHC‐catalyzed reactions, highlighting their efficiency rapid complex We also provide our perspectives on future dynamic highly active research area.

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

25

Phosphine‐Catalyzed Divergent γ,γ‐ and ε,γ‐Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All‐Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids DOI Open Access
Yufei Zhang, Jing Chen, Hui Yao

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 25, 2025

Comprehensive Summary Vicinal all‐carbon quaternary stereocenters are widely present in natural products and bioactive molecules. However, the construction of such motif one step from readily available starting materials remains a significant challenge. Herein, we report phosphine‐catalyzed divergent γ,γ‐ ε,γ‐umpolung domino addition bisoxindoles with allenoates. This method serves as practical tool for concise synthesis series bisoxindole derivatives bearing sterically hindered vicinal under mild reaction conditions. The applicability this novel was demonstrated gram‐scale three known advanced intermediates total syntheses calycanthine, chimonanthine folicanthine.

Language: Английский

Citations

4

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2762 - 2767

Published: Jan. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Language: Английский

Citations

10

Facile synthesis of 2-vinylindolines via a phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process DOI

Shu‐Hui Li,

Dan Xu,

Hui Yao

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(53), P. 6773 - 6776

Published: Jan. 1, 2024

A novel phosphine-mediated α-umpolung/Wittig olefination/cyclization cascade process between o -aminobenzaldehydes and Morita–Baylis–Hillman (MBH) carbonates has been ingeniously developed for the facile synthesis of a broad range 2-vinylindolines.

Language: Английский

Citations

7

NHC-mediated photocatalytic para-selective C–H acylation of aryl alcohols: regioselectivity control via remote radical spiro cyclization DOI

Tinglei Zhang,

Lei Wang,

Xiaolin Peng

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

Language: Английский

Citations

1

Photocatalytic C(sp3)‐H gem‐Difluoroallylation and Alkylation with Alkenes via a Base‐Assisted Formal 1,2‐Hydrogen Atom Transfer of Amidyl Radicals DOI

Meifang Tang,

Bingbing Feng,

Yanyang Bao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2203 - 2210

Published: May 14, 2024

Comprehensive Summary Compared to well‐established 1,5‐HAT of N ‐centered radicals, the synthetic applications 1,2‐HAT process were scarce due high barrier and constrained three‐membered transition state. Here, we have developed a novel C(sp 3 )‐H gem ‐difluoroallylation via base assisted formal amidyl radicals with reductive quenching cycle photocatalyst. This transformation enables efficient formation α‐aminoalkyl showcases good functional group tolerance. Our preliminary mechanistic experiments, along Density Functional Theory (DFT) calculations demonstrate feasibility especially when by base. Furthermore, our method also succeeds in Giese addition electron‐deficient alkenes as well styrene.

Language: Английский

Citations

5

Decatungstate Catalyzed Benzylic C−H Trifluoromethylthiolation DOI

Meifang Tang,

Yanyang Bao,

Han Zhang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(26)

Published: May 22, 2024

Abstract Here we report a mild protocol for benzylic C−H trifluoromethylthiolation using sodium decatungstate (NaDT) as the photocatalyst. Wherein, photoactivated DT abstracted hydrogen atom via radical process. This transformation works well with slight excess of substrates or limiting reagents better purification. The reaction shows conditions and good functional group tolerance. Moreover, could be applied to gram‐scale synthesis.

Language: Английский

Citations

4

Hybrid Palladium-Catalyzed Intramolecular Carboamination of Conjugated Dienes: Synthesis of Functionalized Pyrrolidines via Selective Trifluoromethylarene Defluorination DOI

Feijie Zhang,

Guocong Zhang,

Qixin Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7790 - 7794

Published: May 29, 2024

The incorporation of difluoromethylene groups into aza-heterocycles represents a compelling yet underexplored avenue in contemporary chemical research. In this study, we unveil hybrid palladium-catalyzed intramolecular gem-difluoroalkylamination conjugated dienes, providing versatile approach to the synthesis diverse functionalized pyrrolidines. Noteworthy features include mild reaction conditions and remarkable tolerance toward various functional groups. Additionally, use alkyl iodides as electrophiles facilitates generation corresponding alkylamination products. Control experiments support proposed radical–polar crossover pathway, offering insights underlying processes governing transformation.

Language: Английский

Citations

4

Recent progress in transition metal complexes featuring silylene as ligands DOI Creative Commons
Zohreh Hendi, Madhusudan K. Pandey, Saroj Kumar Kushvaha

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(71), P. 9483 - 9512

Published: Jan. 1, 2024

This review highlights recent advances in transition metal complexes of silylene, showcasing their efficacy hydroboration, hydrosilylation, hydrogenation, hydrogen isotope exchange, and small molecule activation chemistry.

Language: Английский

Citations

4

Controllable Phosphine-Catalyzed Three-Component Domino Reaction of Activated Alkenes with Morita–Baylis–Hillman (MBH) Carbonates: Divergent Synthesis of Densely Functionalized Cyclopentanes and Diquinanes DOI

Yi Li,

Xianfei Hu,

Boning Li

et al.

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

Published: Dec. 7, 2024

An unexpected phosphine-catalyzed controllable three-component domino reaction involving [1 + 2 2] annulation and 2]/[3 sequential of 2-arylmethylidene cyanoacetates/malononitriles with Morita-Baylis-Hillman (MBH) carbonates has been developed. A broad range densely functionalized cyclopentanes diquinanes bearing five or four consecutive stereogenic centers, including two all-carbon quaternary stereocenters, were smoothly acquired in moderate to excellent yields under mild conditions from readily available materials. Moreover, this divergent transformation enables the simultaneous generation three new C-C bonds one carbocyclic rings only step.

Language: Английский

Citations

4