Site‐Selective Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis

Abstract We herein disclose a protocol for linear‐selective ring‐opening acylation of a range of electron‐poor VCPs with α‐ketoacids by Ir‐photocatalyst. While electron‐poor VCPs could be sensitized with various radical species generated under different reaction conditions including photo‐redox processes, exploring similar repertoire with acyl radical remains unexplored. Since the linear selective ring opening leads to translocation of the vinylic olefin into an internal one, terminal addition of VCP systems with electronically diverse groups present at the terminus, permitting formation of tailored of building blocks.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-10-17
DOI
https://doi.org/10.1002/ajoc.202400325
Citations
3
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.75

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article

Site‐Selective Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis

Chenna Jagadeesh, Anand B. Melkani, Jaideep Saha, S. Mondal et al.
3 citations
Asian Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
0.75
article

Site‐Selective Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis

Chenna Jagadeesh, Anand B. Melkani, Jaideep Saha, S. Mondal, Subhadeep Hazra, Manveer Patel
article en
3 citations

Abstract

Abstract We herein disclose a protocol for linear‐selective ring‐opening acylation of a range of electron‐poor VCPs with α‐ketoacids by Ir‐photocatalyst. While electron‐poor VCPs could be sensitized with various radical species generated under different reaction conditions including photo‐redox processes, exploring similar repertoire with acyl radical remains unexplored. Since the linear selective ring opening leads to translocation of the vinylic olefin into an internal one, terminal addition of VCP systems with electronically diverse groups present at the terminus, permitting formation of tailored of building blocks.

Asian Journal of Organic ChemistryVol. 14(1)
Kumaun University (IN), National Institute of Pharmaceutical Education and Research - Ahmedabad (IN), Synthetic Biologics (United States) (US), National Institute of Pharmaceutical Education and Research (IN), Centre of Biomedical Research (IN)
Science and Engineering Research Board
Openalex Percentile: Top 32%
Cyclopropane Reaction Mechanisms
0.75
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Site‐Selective Acylation of Vinylcyclopropanes under Visible‐Light Photocatalysis — Chenna Jagadeesh, Anand B. Melkani, et al. · Asian Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS