Synthesis of 6 H-Benzo[c]chromene Scaffolds: A Synthetic Strategy of Pd-Catalyzed Annulation Followed by Aerial Oxidation

Kangkana Chutia; Priyanka Saikia; Dhiraj Dutta; Babulal Das; Pranjal Gogoi

doi:10.1021/acs.joc.4c02780

Synthesis of 6 H-Benzo[c]chromene Scaffolds: A Synthetic Strategy of Pd-Catalyzed Annulation Followed by Aerial Oxidation

J Org Chem. 2025 Jan 3. doi: 10.1021/acs.joc.4c02780. Online ahead of print.

Authors

Kangkana Chutia^{1

2}, Priyanka Saikia¹, Dhiraj Dutta¹, Babulal Das³, Pranjal Gogoi^{1

2}

Affiliations

¹ Applied Organic Chemistry Group, Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India.
² Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
³ Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.

PMID: 39752258
DOI: 10.1021/acs.joc.4c02780

Abstract

A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6H-benzo[c]chromene scaffolds. Various 6H-benzo[c]chromenes were synthesized under mild reaction conditions using easily accessible p-QMs and commercially available o-hydroxyarylboronic acids. One of the synthesized chromenes has been ambiguously confirmed by single-crystal XRD analysis. Interestingly, our synthesized 6H-benzo[c]chromenes could be easily transformed into valuable 6H-benzo[c]chromen-6-ones via aerial oxidation.