A General Approach for the Synthesis of Cyanoisopropyl Bicyclo[1.1.1]pentane (BCP) Motifs by Energy Transfer Process

• Published in: Organic letters Vol. 26; no. 33; pp. 7060 - 7065
• Main Authors: Li, Lin, Pang, Qing, Chen, Binbin, Liu, Yumiao, Zhao, Yuxuan, Wu, Jirong, Ge, Kai, Shen, Jiabin, Zhang, Pengfei
• Format: Journal Article
• Language: English
• Published: American Chemical Society 23.08.2024
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/acs.orglett.4c02674

Bicyclo­[1.1.1]­pentane (BCP) heteroaryls make up an important class of BCP derivatives in drug discovery. Herein, we report the visible-light-mediated synthesis of cyanoisopropyl BCP-heteroaryls motifs from N-containing heterocycles, [1.1.1]­propellane, and AIBN (2,2′-azobis­(isobutyronitrile)) through three-component cascade reaction. Importantly, this protocol is compatible with pyrazinones, quinoxaline-2­(1H)-one, azauracils, quinoline derivatives, and imidazo­[1,2-b]­pyridazine, as well as various phenyl disulfide derivatives; thus, this operationally simple and general methodology could enable rapid library generation of sought-after BCP derivatives for drug development.