Visible‐Light‐Mediated Synthesis of α‐Ketoamides via Oxidative Amination of 2‐Bromoacetophenones Using Eosin Y as a Photoredox Catalyst DOI

Kaushal Kishor,

Neha Sharma Prabhakar,

Krishna Nand Singh

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(19)

Published: Aug. 29, 2023

An oxidative amination of 2-bromoacetophenones has been accomplished to provide α-ketoamides by using photoredox catalysis with air as oxidant. The reactants are readily accessible, and the method is endowed broad substrate scope good functional group tolerance. practicality approach also shown a gram-scale reaction.

Language: Английский

De Novo Synthesis of α‐Ketoamides via Pd/TBD Synergistic Catalysis DOI Creative Commons
Jiahe Chen,

Li‐Ren Zhang,

Zhang‐Yang Wang

et al.

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

Published: July 10, 2024

Precisely controlling the product selectivity of a reaction is an important objective in organic synthesis. α-Ketoamides are vital intermediates chemical transformations and privileged motifs numerous drugs, natural products, biologically active molecules. The selective synthesis α-ketoamides from feedstock chemicals safe operationally simple manner under mild conditions long-standing catalysis challenge. Herein, unprecedented TBD-switched Pd-catalyzed double isocyanide insertion for assembling ketoamides aqueous DMSO (hetero)aryl halides pseudohalides reported. effectiveness utility this protocol demonstrated by its diverse substrate scope (93 examples), ability to late-stage modify pharmaceuticals, scalability large-scale synthesis, pharmaceutically Mechanistic studies indicate that TBD key ligand modulates process, thereby selectively providing desired unique manner. In addition, imidoylpalladium(II) complex α-ketoimine amide successfully isolated determined X-ray analysis, confirming they probable catalytic pathway.

Language: Английский

Citations

2
Easy Access to α-Ketothioamides via Oxidative Amidation of Bunte Salts Using Electrolysis or Hypervalent Iodine DOI

Neha Sharma Prabhakar,

Kaushal Kishor,

Krishna Nand Singh

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13329 - 13337

Published: Sept. 10, 2024

Two new protocols leveraging electrochemical and hypervalent iodine-mediated synthesis of α-ketothioamides have been developed by using easily accessible cost-effective Bunte salts secondary amines. The methods are efficient, simple, straightforward, showcase the formation C-N bonds across diverse substrates under ambient conditions.

Language: Английский

Citations

2
Modular Synthesis of Divergent Thiofunctionalized Sulfoxonium Ylides DOI

Qiong Hu,

Mei-Zhu Bao,

Yuanjie Meng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A metal-free protocol for the modular synthesis of diverse α-thiofunctionalized-α′-carbonyl sulfoxonium ylides from sulfoxonium–iodonium hybrid (I (III) /S (VI) -ylides) has been achieved.

Language: Английский

Citations

2
I2‐DMSO‐Mediated Cascade Cyclization of β‐Ketosulfoxonium Ylides and β‐Enaminones: Synthesis of Quaternary‐Carbon‐Centered 2‐Hydroxy‐pyrrol‐3(2H)‐ones DOI

Rahul Kumar Saini,

Paran J. Borpatra, Satyendra Kumar Pandey

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(37)

Published: July 19, 2023

Abstract A novel I 2 ‐DMSO‐mediated cascade cyclization approach for synthesizing 2‐hydroxy‐pyrrol‐3(2 H )‐one scaffold from readily accessible β ‐ketosulfoxonium ylides and ‐enaminone derivatives has been developed. Under metal‐free mild conditions, this transformation facilitates the formation of one C−C bond C−N in a single reaction vessel, exhibiting wide range functional group compatibility. In addition, method added an active hydroxyl to quaternary carbon center.

Language: Английский

Citations

4
Visible‐Light‐Mediated Synthesis of α‐Ketoamides via Oxidative Amination of 2‐Bromoacetophenones Using Eosin Y as a Photoredox Catalyst DOI

Kaushal Kishor,

Neha Sharma Prabhakar,

Krishna Nand Singh

et al.

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(19)

Published: Aug. 29, 2023

An oxidative amination of 2-bromoacetophenones has been accomplished to provide α-ketoamides by using photoredox catalysis with air as oxidant. The reactants are readily accessible, and the method is endowed broad substrate scope good functional group tolerance. practicality approach also shown a gram-scale reaction.

Language: Английский

Citations

4