Zou Wen-Xuan, Hu Qiong, Shen Dan-Ting, Wu Wen-Rong, Wei Jiaohang, Yang Zi-Feng, Bao Mei-Zhu, Liu Xiang, Zhang Shang-Shi
Center for Drug Research and Development, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. China.
School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, P. R. China.
Org Lett. 2024 Jul 12;26(27):5811-5816. doi: 10.1021/acs.orglett.4c02000. Epub 2024 Jun 28.
A practical strategy for the construction of diverse phosphonyl and thiofunctionalized sulfoxonium ylides via controllable monofunctionalization of hybrid I/S ylides is presented. This process allows efficient P-H insertion of I/S ylides under Cu catalysis, enabling the synthesis of phosphonyl sulfoxonium ylides, whereas reaction with sulfur-containing reagents including AgSCF, KSC(S)OR, and KSCN under mild conditions resulted in α-trifluoromethylthiolation, dithiocarbanation, and thiocyanation of sulfoxonium ylides accordingly. Of note, wide substrate compatibility (108 examples), excellent efficiency (up to 99% yield), gram-scale experiments, and various product derivatizations highlight the synthetic utility of this protocol.
本文提出了一种实用策略，通过杂化I/S叶立德的可控单官能化构建多种膦酰基和硫官能化的硫鎓叶立德。该过程允许在铜催化下I/S叶立德进行高效的P-H插入反应，从而实现膦酰基硫鎓叶立德的合成，而在温和条件下与含硫试剂（包括AgSCF、KSC(S)OR和KSCN）反应，则相应地导致硫鎓叶立德的α-三氟甲基硫代化、二硫代碳酸酯化和硫氰化反应。值得注意的是，广泛的底物兼容性（108个实例）、出色的效率（高达99%的产率）、克级实验以及各种产物衍生化突出了该方法的合成实用性。
