文献类型：期刊文献

英文题名：Visible-light induced metal-free intramolecular reductive cyclisations of ketones with alkynes and allenes

作者：Tang, Nana[1];Zachmann, Raphael J.[1];Xie, Hui[1];Zheng, Jun[2,3];Breit, Bernhard[1]

机构：[1]Albert Ludwigs Univ Freiburg, Inst Organ Chem, Albertstr 21, D-79104 Freiburg, Germany;[2]Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2023

卷号：59

期号：15

起止页码：2122

外文期刊名：CHEMICAL COMMUNICATIONS

收录：;EI(收录号：20230713580112);WOS:【SCI-EXPANDED(收录号:WOS:000926906900001)，CCR-EXPANDED(收录号:WOS:000926906900001)】；

语种：英文

外文关键词：Cyclization - Hydrocarbons

摘要：A visible-light-induced, intramolecular, reductive cyclisation of ketones with an unsaturated hydrocarbon moiety was developed. In contrast to conventional protocols requiring resource precious or hazardous metal sources, this method enables facile access to ketyl radicals under metal-free and mild reaction conditions. By polarity-reversed, ketyl radical hydroalkoxylation of alkynes and allenes, a variety of five-membered (hetero-)cyclic products were generated in good yields with good to excellent stereoselectivities. The embedded homoallylic tertiary alcohol could be transformed into other useful functionalities, highlighting the synthetic utility of this reaction. This efficient and sustainable ketyl-alkyne/allene cross coupling also features broad functional group tolerance and scalability.