Complexity-Building Photoinduced Cascade Involving Csp2-Csp3 Coupling of Aromatic Amides via [2 + 2] Reactivity of ESIPT-Generated o- Azaxylylenes

D Sai Reddy; Ivan M Novitskiy; Andrei G Kutateladze

doi:10.1021/acs.orglett.3c00092

Complexity-Building Photoinduced Cascade Involving C_sp²-C_sp³ Coupling of Aromatic Amides via [2 + 2] Reactivity of ESIPT-Generated o- Azaxylylenes

Org Lett. 2023 Feb 24;25(7):1131-1135. doi: 10.1021/acs.orglett.3c00092. Epub 2023 Feb 10.

Authors

D Sai Reddy¹, Ivan M Novitskiy¹, Andrei G Kutateladze¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of Denver, Denver, Colorado 80208, United States.

PMID: 36763986
DOI: 10.1021/acs.orglett.3c00092

Abstract

A new mode for complexity-building photochemical cascades which offers experimentally simple transition metal-free intramolecular C_sp²-C_sp³ cross coupling of aromatic amides is attained via an unprecedented [2 + 2] reactivity of ESIPT-generated azaxylylenes. Coupled with short and straightforward postphotochemical modifications of the primary photoproducts, these cascades allow for a significant step-normalized growth of molecular complexity while accessing diverse and complex polyheterocyclic molecular architectures.