碱调节的磺酰基吲哚的膦氢化反应  

Base-mediated Hydrophosphinylation of Sulfonyl Indoles

作　　者：贾云清 王浩宇[1] 葛真真 周鸣强[1] 赵建强[1] 袁伟成[1] JIA Yunqing;WANG Haoyu;GE Zhenzhen;ZHOU Mingqiang;ZHAO Jianqiang;YUAN Weicheng(National Engineering Research Center of Chiral Drugs,Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041,China;University of Chinese Academy of Sciences,Beijing 100049,China)

机构地区：[1]中国科学院成都有机化学研究所手性药物国家工程研究中心,四川成都610041 [2]中国科学院大学,北京100049

出　　处：《合成化学》2023年第10期779-784,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(22171029,21901024,21871252,21801024,21801026)。

摘　　要：含磷吲哚衍生物是一类重要的有机磷化合物,不仅广泛存在于医药制剂中,而且作为配体和中间体广泛存在于材料学和有机合成中。利用膦亲核试剂对磺酰吲哚原位生成的插烯亚胺中间体进行迈克尔加成,能够以较高收率得到一系列3-膦取代吲哚化合物。以磺酰基吲哚和二苯基氧磷为原料,在无机碱碳酸铯作用下发生迈克尔加成反应,合成了11个结构新颖的3-(1-磷酰基)甲基吲哚类化合物3a~3k,产率为72%~98%,并对这些化合物进行^(1)H NMR、^(13)C NMR、31 P NMR、熔点和HR-MS(ESI-TOF)表征。Phosphoindole derivatives are an important class of organophosphorus compounds,which not only widely exist in pharmaceutical preparations,but also widely exist as ligands and intermediates in materials science and organic synthesis.A series of 3-phosphine substituted indole compounds can be obtained in high yield by Michael addition of intercalated imine intermediates generated in situ using phosphine nucleophiles.In this paper,we reported the Michael addition of diphenylphosphine oxide to vinylogous imine intermediates in situ generated from sulfonyl indoles with Cs_(2)CO_(3)as the base.Eleven structurally diverse 3-(1-diphenylphosphoryl-arylmethyl)indoles 3a~3k were obtained with high yields ranging from 72%to 98%.These compounds were characterized by^(1)H NMR,^(13)C NMR,31 P NMR,melting point and HR-MS(ESI-TOF).

关 键 词：含膦吲哚衍生物 磺酰基吲哚 插烯亚胺中间体 二苯基氧磷 迈克尔加成 膦氢化 

分 类 号：O621.3[理学—有机化学]