Construction of C–S and C–Se Bonds via Photocatalytic Aromatization-Driven Deconstructive Diversification of Spiro-Dihydroquinazolinones Derived from Unstrained Ketones
Tao Wang, Jin‐Long Dai, Yifeng Jiang, Shenghu Yan, Jia‐Yin Wang
Abstract
A novel and robust deconstructive functionalization reaction of spiro-dihydroquinazolinones with sulfenylating reagents in the presence of base has been realized under visible light irradiation. This reaction enabled the direct ring-opening of unstrained cyclic ring systems, producing skeletally diverse functionalized quinazolinones with moderate to good yields. A range variety of sulfenylating reagents including diaryl disulfide, thiosulfonate, dithiosulfonate and 1-[(trifluoromethyl)thio]-2,5-pyrrolidinedione were compatible for this transformation. In addition, diaryl diselenide and selenosulfonate could also couple with spiro -dihydroquinazolinones to form C–Se Bonds. Mechanistic studies revealed that the reaction proceeds via a radical–radical coupling pathway.