Yang Wen-Peng, Miao Hong-Jie, Liu Le, Duan Xin-Hua, Guo Li-Na
Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy Storage, Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.
Org Lett. 2024 Sep 6;26(35):7442-7446. doi: 10.1021/acs.orglett.4c02793. Epub 2024 Aug 26.
A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3)-ones in good yields with excellent functional group tolerance. A radical pathway involving C-C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.
本文报道了一种可见光促进的螺环碳环芳烃化驱动的解构氟化反应。一系列螺二氢喹唑啉酮在可见光照射下与NFSI高效反应，以良好的产率得到2-(4-氟烷基)喹唑啉-4(3)-酮，且具有优异的官能团耐受性。该反应提出了一种涉及C-C键断裂和F原子转移的自由基途径。此外，螺二氢喹唑啉酮与NCS的开环氯化反应也适用。
