Electron donor-acceptor complex enabled photocascade strategy for the synthesis of trans-dihydrofuro[3,2- c]chromen-4-one scaffolds via radical conjugate addition of pyridinium ylide

Sovan Dey; Arindam Das; Ram Naresh Yadav; Palash Jyoti Boruah; Koushik Sarkar; Amit Kumar Paul; Md Firoj Hossain

doi:10.1039/d4cc04720f

Electron donor-acceptor complex enabled photocascade strategy for the synthesis of trans-dihydrofuro[3,2- c]chromen-4-one scaffolds via radical conjugate addition of pyridinium ylide

Chem Commun (Camb). 2024 Dec 3;60(97):14384-14387. doi: 10.1039/d4cc04720f.

Authors

Sovan Dey¹, Arindam Das¹, Ram Naresh Yadav², Palash Jyoti Boruah³, Koushik Sarkar⁴, Amit Kumar Paul⁵, Md Firoj Hossain¹

Affiliations

¹ Department of Chemistry, University of North Bengal, Raja Rammohunpur, Darjeeling-734013, India. [email protected].
² Department of Chemistry, Faculty of Engineering and Technology, Veer Bahadur Singh Purvanchal University, Jaunpur-222003, UP, India.
³ Department of Chemistry, NIT, Meghalaya, Shillong-793003, India.
⁴ Department of Chemical Sciences, IISER Kolkata, Mohanpur-741246, Nadia, WB, India.
⁵ Bose Institute, Unified Academic Campus, EN 80, Sector V, Salt Lake, Kolkata-700091, India.

PMID: 39450510
DOI: 10.1039/d4cc04720f

Abstract

A visible-light-induced photocascade strategy is disclosed for the synthesis of trans-dihydrofuro[3,2-c]chromen-4-one scaffolds. The photocascade consists of electron donor-acceptor (EDA) complex enabled formation of arylidene coumarinone, followed by 1,4-radical conjugate addition (1,4-RCA) of an in situ generated pyridinium ylide radical (PyYR) towards diastereoselective formation of the trans-dihydrofuro[3,2-c]chromen-4-one scaffold in good to excellent yield. Thorough mechanistic investigations comprising photophysical, spectroscopic, electrochemical and DFT studies provide further insights into the reaction mechanism.