Cobalt-Catalyzed Deacylative Ipso-C-C Bond Functionalization: An Approach toward Indole-Acyloins and Its Photophysical Studies

Shyam Kumar Banjare, Saista Afreen, Wang Yeuk Kong, Wentao Guo, Tanmayee Nanda, Gopal Krushna Das Adhikari, Naupada Preeyanka, Dean J. Tantillo*, Ponneri C. Ravikumar*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Selective functionalization of the indole-C3-C bond with aromatic/heteroaromatic 1,2-diketones has been uncovered for the first time. Cobalt catalyst was found to be an effective catalyst for this unusual transformation. This ipso-C-C bond functionalization occurred in the presence of easily available weakly coordinating groups such as ketone and ester. One of the salient features of this methodology is the in situ generation of water from hexafluoro-2-propanol which acts as a reactant for the removal of the pivaloyl/ester group in a deacylative manner. The plausible mechanism has been supported by DFT calculations. Moreover, photophysical studies show the potential utility of indole-C3-acyloin and indolo-fused carbazole, which could be used in photovoltaic and optoelectronic application.

Original languageEnglish
Pages (from-to)9187-9197
Number of pages11
JournalJournal of Organic Chemistry
Volume89
Issue number13
Early online date21 Jun 2024
DOIs
Publication statusPublished - 5 Jul 2024
Externally publishedYes

Funding

Publisher Copyright: © 2024 American Chemical Society.

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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