Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates

Hisham Qrareya; Lorenzo Meazza; Stefano Protti; Maurizio Fagnoni

doi:10.3762/bjoc.16.250

Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates

Beilstein J Org Chem. 2020 Dec 8:16:3008-3014. doi: 10.3762/bjoc.16.250. eCollection 2020.

Authors

Hisham Qrareya^{1

2}, Lorenzo Meazza¹, Stefano Protti¹, Maurizio Fagnoni¹

Affiliations

¹ PhotoGreen Lab, Department of Chemistry, viale Taramelli 12, 27100 Pavia, Italy.
² Industrial Chemistry Department, Arab American University, 240 Jenin 13, Zababdeh, Palestine.

Abstract

A metal-free route for the synthesis of biarenes has been developed. The approach is based on the photoextrusion of a phosphate moiety occurring upon irradiation of biaryl- and triaryl phosphates. The reaction involves an exciplex as the intermediate and it is especially suitable for the preparation of electron-rich biarenes.

Keywords: aryl phosphates; biarenes; metal-free synthesis; photochemistry; photoextrusion.

Grants and funding

H. Q. thanks the Arab American University-Palestine (AAUP) for financial support, and the University of Pavia (Italy) for hosting.