Cobalt-catalyzed regioselective (4+2)-annulation of benzamides with allenyl carbinol acetates: access to 3-vinylisoquinolinones

Herein, we disclose a Co-catalyzed regioselective (4+2)-annulation of aryl-, heteroaryl- and acrylamides with allenyl acetates to access a diverse array of heterocyclic derivatives in high yields with excellent regioselectivity. The protocol employs inexpensive cobalt(II) salts and exhibits broad functional group tolerance. Solvent plays a crucial role in governing regioselective migratory insertion, facilitating the selective formation of the elusive Co-alkenyl intermediate. Preliminary mechanistic experiments were performed to elucidate the plausible reaction pathway.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc04210k
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

Cobalt-catalyzed regioselective (4+2)-annulation of benzamides with allenyl carbinol acetates: access to 3-vinylisoquinolinones

Pravin Kumar
1 citations
Chemical Communications
Catalytic C–H Functionalization Methods
0.94
article

Cobalt-catalyzed regioselective (4+2)-annulation of benzamides with allenyl carbinol acetates: access to 3-vinylisoquinolinones

Pravin Kumar
article en
1 citations

Abstract

Herein, we disclose a Co-catalyzed regioselective (4+2)-annulation of aryl-, heteroaryl- and acrylamides with allenyl acetates to access a diverse array of heterocyclic derivatives in high yields with excellent regioselectivity. The protocol employs inexpensive cobalt(II) salts and exhibits broad functional group tolerance. Solvent plays a crucial role in governing regioselective migratory insertion, facilitating the selective formation of the elusive Co-alkenyl intermediate. Preliminary mechanistic experiments were performed to elucidate the plausible reaction pathway.

Chemical CommunicationsVol. 61(87)
Indian Institute of Technology Bombay (IN)
Openalex Percentile: Top 21%
Catalytic C–H Functionalization Methods
0.94
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