Site-Specific Radical Alkylation of Aryl Cyanide: Visible-Light, Photoredox-Catalyzed, Three-Component Arylalkylation of 1.1.1Propellane

• Published in: Organic letters 2024-09, Vol.26 (36), p.7769
• Main Authors: Hou, Hong, Guo, Shengkun, Shen, Xiaoyu, Chen, Chengjun, Chen, Xiaoyun, Yu, Huaguang, Han, Ying, Sun, Qiu, Zhu, Shaoqun
• Format: Article
• Language: English
• ISSN: 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.4c02969

We report herein a three-component radical arylalkylation of [1.1.1]propellane toward the synthesis of aryl-substituted bicyclo[1.1.1]pentane derivatives. The use of electron-deficient aryl cyanide as an aryl group source not only reduces the energy barrier of the arylation of the nucleophilic alkyl radical species, but also suppresses the electrophilic Friedel-Crafts alkylation process, enabling the present site-selective arylalkylation.We report herein a three-component radical arylalkylation of [1.1.1]propellane toward the synthesis of aryl-substituted bicyclo[1.1.1]pentane derivatives. The use of electron-deficient aryl cyanide as an aryl group source not only reduces the energy barrier of the arylation of the nucleophilic alkyl radical species, but also suppresses the electrophilic Friedel-Crafts alkylation process, enabling the present site-selective arylalkylation.