Co(III)-Catalyzed Regioselective Functionalization of Isoquinolones with Naphthoquinones.

Org Lett

C-H Activation and Phytochemistry Lab, Chemical Technology Division, CSIR-IHBT, Palampur 176061, India.

Published: June 2024

AI Article Synopsis

  • A novel method has been introduced for Co(III)-catalyzed C(sp)-H alkenylation, targeting less reactive -protected isoquinolones with 1,4-naphthoquinones.
  • The protocol is effective for a variety of isoquinolone substitutions, and studies suggest a five-membered cobaltacycle is formed as an intermediate, indicating a unique reaction pathway.
  • The scalability of the reaction has been demonstrated, and the resulting product was successfully used as a chemosensor to detect iron ions.

Article Abstract

A strategy for Co(III)-catalyzed C(sp)-H alkenylation of -protected isoquinolones with 1,4-naphthoquinones has been disclosed. The developed protocol was efficiently applied for diversely substituted isoquinolones. Preliminary mechanistic experiments revealed the involvement of a five-membered cobaltacycle as an intermediate. Deuterium labeling experiments suggested the reversible nature of the C-H activation step. The scale-up reaction was also carried out, and the product was utilized as a chemosensor to detect Fe ions.

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Source
http://dx.doi.org/10.1021/acs.orglett.4c01686DOI Listing

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