Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
Org Lett. 2023 Feb 17;25(6):1014-1019. doi: 10.1021/acs.orglett.3c00182. Epub 2023 Feb 6.
Alkyl sulfonamides are an important class of bioactive molecules. Historical syntheses have relied on multistep sequences incorporating harsh reaction conditions. Photochemical methods have been limited to hydrosulfamoylation, installing only one substituent across an olefin. Herein, radical/polar crossover (RPC) is used to establish the first multicomponent 1,2-difunctionalization reaction incorporating a sulfonamide moiety and a second reaction partner. This protocol, exemplified on a range of olefins, utilizes various commercial sulfamoyl chlorides and organotrifluoroborates as coupling partners.
烷基磺酰胺是一类重要的生物活性分子。历史合成依赖于多步序列，其中包含苛刻的反应条件。光化学方法仅限于氢磺酰胺化，只能在烯烃上安装一个取代基。在此，自由基/极性交叉（RPC）被用于建立第一个包含磺酰胺部分和第二个反应伙伴的多组分 1,2-双官能化反应。该方案以一系列烯烃为例，利用各种商业磺酰氯和有机三氟硼酸盐作为偶联伙伴。
