Visible Light Promoted Brominative Dearomatization of Biaryl Ynones to Spirocycles

Abstract

Bromine induced spiro cyclization of biaryl ynones facilitated the synthesis of spiro[5,5]trienones suitable for extended functionality at the C(3′) position. Herein, a step-economic photo-oxidative brominative carbannulation of biaryl ynones employing ammonium bromide and riboflavin tetraacetate (RFTA) has been developed. The reactivity between distal phenyl C-H activated ortho-annulation and dearomative ipso-annulation is well exemplified. The eminent features of the methodology include metal-free, external additive free, low-loading photocatalyst (0.1 mol %), and use of a simple precursor. © 2023 American Chemical Society.