Jiang Yu-Shi, Liu Fu, Huang Miao-Sha, Luo Xue-Ling, Xia Peng-Ju
School of Chemistry and Pharmaceutical Sciences, State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Guangxi 541004, P. R. China.
Org Lett. 2022 Nov 4;24(43):8019-8024. doi: 10.1021/acs.orglett.2c03233. Epub 2022 Oct 20.
The modular cyanoalkylamination of alkenes using bench-stable and easy-to-handle α-imino-oxy acid oxime esters as difunctional reagents creates new synthetic avenues. A metal-free photosensitization protocol for the installation of both amino and cyanoalkyl functionalities onto alkene feedstocks in a single step via two differently reactive nitrogen-centered radicals was developed via energy-transfer catalysis. Excellent functional group tolerance and mild reaction conditions also render this protocol suitable for the cyanoalkylamination of pharmaceutically relevant molecule-derived alkenes.
使用稳定且易于操作的α-亚氨基氧基酸肟酯作为双官能试剂对烯烃进行模块化氰基烷基化反应开辟了新的合成途径。通过能量转移催化，开发了一种无金属光敏反应方案，可通过两个具有不同反应活性的氮中心自由基，将氨基和氰基烷基官能团一步安装到烯烃原料上。出色的官能团耐受性和温和的反应条件也使该方案适用于药物相关分子衍生烯烃的氰基烷基化反应。
