Ru(II)-Catalyzed Redox-Neutral C–H Olefination and Tandem Cyclization with Vinyl Sulfones: Leveraging Sulfinate Anion as a Leaving Group for the Synthesis of 3-Methyleneisoindolin-1-ones DOI

Tamanna Rana,

Amit B. Pawar

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

Published: Dec. 2, 2024

We developed a Ru(II)-catalyzed redox-neutral C–H olefination of N-methoxybenzamides with vinyl sulfones. The reaction is operationally simple and conducted at ambient temperature does not require silver additives or external oxidants, making it suitable for late-stage functionalization. Notably, we leveraged the leaving group ability sulfinate anion to synthesize 3-methyleneisoindolin-1-ones through tandem olefination/cyclization/elimination sequence temperature. Moreover, successfully demonstrated synthetic versatility 3-methyleneisoindolin-1-one construction an isoindolobenzazepine core.

Language: Английский

Electrophilic hexa(methoxycarbonyl)cycloheptatrienyl anion in the synthesis of electron-deficient 5-hydroxyisoquinolones DOI

Alexander Yu. Belyy,

Alena D. Sokolova,

Rinat F. Salikov

et al.

Mendeleev Communications, Journal Year: 2025, Volume and Issue: 35(2), P. 162 - 164

Published: Jan. 1, 2025

Language: Английский

Citations

1

Palladium-catalyzed denitrogenation/vinylation of benzotriazinones with vinylene carbonate DOI
Jiang Nan, Qiong Huang,

Xinran Men

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(26), P. 3571 - 3574

Published: Jan. 1, 2024

Herein, a novel Pd-catalyzed denitrogenation/vinylation of benzotriazinones using vinylene carbonate as the vinylation reagent is reported. This transformation demonstrates an unprecedented skeletal editing approach, effectively converting NN to CC fragments

Language: Английский

Citations

5

Harnessing Dual Reactivity of N-Chloroamides for Cascade C–H Amidation/Chlorination of Indoles under Cobalt-Catalysis: Overriding Hofmann Rearrangement Pathway Leading to Aminocarbonylation DOI

Vinod V. Nagesh,

Amit B. Pawar

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

Published: Nov. 27, 2024

Herein, we have developed a Cp*Co(III)-catalyzed cascade C-2 amidation/C-3 chlorination of indoles by leveraging the dual functionality

Language: Английский

Citations

3

Progress on Cobalt-Catalyzed C(sp2)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles DOI
Xun Tian, Guogang Deng, Xiaodong Yang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 655 - 655

Published: Jan. 1, 2025

Language: Английский

Citations

0

Palladium‐Catalyzed [3+2+1]/[4+2] Heteroannulation of Allylamines with CO and 1,4‐Enynes Leading to 1,7,8,8a‐Tetrahydroisoquinolin‐3(2H)‐ones DOI
Xue Qi, Yang Li,

Fujin Sun

et al.

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

Published: April 25, 2025

Comprehensive Summary Aminocarbonylative heteroannulation of unsaturated hydrocarbons with amines and CO has become a key transformation in organic synthesis to build N ‐heterocycles. In this report, new palladium‐catalyzed aminocarbonylative [3+2+1]/[4+2] allylamines 4‐en‐1‐yn‐3‐yl acetates for the 1,7,8,8a‐tetrahydroisoquinolin‐3(2 H )‐ones been developed. The method enables construction two six‐membered rings single reaction step leading formation isoquinolinone scaffolds, featuring excellent selectivity, good functional group compatibility broad substrate scope. A possible mechanism involving Pd‐catalyzed isomerization form allenyl‐Pd intermediate, aminocarbonylation cycloaddition was proposed.

Language: Английский

Citations

0

Harnessing sulfilimine as an oxidizing directing group in Cp*Co(iii)-catalyzed [4+2] annulation with alkynes and 1,3-diynes DOI Creative Commons
Arijit Ghosh, Amit B. Pawar

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

Published: Jan. 1, 2025

Herein, we report the first Cp*Co( iii )-catalyzed redox-neutral [4 + 2] C–H annulation employing sulfilimine as an oxidizing directing group, wherein N–S bond serves internal oxidant.

Language: Английский

Citations

0

Photoredox Catalyzed Tandem Denitrogenative [4 + 2] Annulation of 1,2,3-Benzotriazin-4(3H)-ones with Terminal Olefins DOI
Haiqiong Li, Liang Yu,

Fen Han

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 16043 - 16048

Published: Oct. 15, 2024

The dihydroisoquinolones skeleton is ubiquitous in natural products and biological molecules. Reported strategies for constructing usually require noble metal catalysts or stoichiometric oxidants, which limit their wide applications. Herein, we developed a photoredox catalyzed tandem denitrogenative [4 + 2] annulation reaction of 1,2,3-benzotriazin-4(3H)-ones with terminal olefins. A variety can be accessed moderate to excellent yield. This protocol features high atom-economy, mild conditions, external oxidant-free, enabling the synthesis various substituted dihydroisoquinolones.

Language: Английский

Citations

1

Recent Advances in Nonprecious Metal Catalysis DOI
David J. Bernhardson, Aran K. Hubbell, Robert A. Singer

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 7, 2024

As the field of nonprecious metal catalysis continues to expand, we pursue a review series covering selected transformations in this area over short time interval highlight practical advancements. We seek raise awareness both current art and need continue development toward broader applications earth-abundant metals chemical pharmaceutical industries.

Language: Английский

Citations

1

Ru-Catalyzed Redox-Neutral Coupling of N-Chlorobenzamides with Unsymmetrical Alkynes in Water DOI
Sharajit Saha, Hemanga Bhattacharyya,

Subhankar Dolai

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16850 - 16864

Published: Oct. 24, 2024

In water, Ru-catalyzed annulation of

Language: Английский

Citations

0

Redox-neutral access to isoquinolines via cobalt(III)-catalyzed C H acylmethylation/cyclization of benzimidates with sulfoxonium ylides DOI
Min Li, Zhenhai Xia,

Lixing Tang

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 146, P. 155185 - 155185

Published: July 7, 2024

Language: Английский

Citations

0