新型氮杂环卡宾催化剂的合成及其在烯烃的自由基氟烷基酰化反应中的应用研究  

Synthesis of Novel N-Heterocyclic Carbene Catalysts and Its Application in Radical Acylfluoroalkylation of Olefins

作　　者：代海渝 戴青松 何美浩 李青竹 杨四琳 田远航 王亚鹏 刘万聪 张翔 李俊龙 王启卫[2,4] DAI Haiyu;DAI Qingsong;HE Meihao;LI Qingzhu;YANG Silin;TIAN Yuanhang;WANG Yapeng;LIU Wancong;ZHANG Xiang;LI Junlong;WANG Qiwei(School of Mechanical Engineering,Chengdu University,Chengdu 610106,China;Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province,Sichuan Industrial Institute of Antibiotics,School of Pharmacy,Chengdu University,Chengdu 610052,China;Chengdu Institute of Organic Chemistry,Chinese Academy of Sciences,Chengdu 610041,China;School of Science,Xihua University,Chengdu 610039,China)

机构地区：[1]成都大学机械工程学院,四川成都610106 [2]成都大学药学院(川抗所)抗生素研究与再评价四川省重点实验室,四川成都610052 [3]中国科学院成都有机化学研究所,四川成都610041 [4]西华大学理学院,四川成都610039

出　　处：《合成化学》2022年第9期681-687,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21871031,22071011);西华大学人才引进项目(Z202084)。

摘　　要：以环庚酮及环己(庚)胺为起始原料,经溴代、环化和脱硫等反应,以良好的收率合成了环烷基取代的新型噻唑骨架的氮杂环卡宾催化剂。结果表明:在该催化剂催化下成功地实现了烯烃的自由基氟烷基酰化反应,并以中等收率完成了三种类型的γ-氟烷基取代酮的高效合成。所得化合物通过^(1)H NMR,^(13)C NMR,^(19)F NMR和HR-MS(ESI-TOF)进行表征。Novel thiazole-based N-heterocyclic carbene(NHC)catalysts with cycloalkyl were synthesized in good yields via bromination,cyclization,desulfurization,etc,using cycloheptanone and cyclo-hexex(-heptyl)amine as the starting material.The radical acylfluoroalkylation of olefins was achieved through the prepared NHC organocatalysis,giving three kinds ofγ-fluoroalkyl ketones with moderate yields.The obtained compounds were characterized by ^(1)H NMR,^(13)C NMR,^(19)F NMR and HR-MS(ESI-TOF).

关 键 词：氮杂环卡宾 噻唑骨架 环烷基 烯烃双官能团化反应 自由基氟烷基酰化反应 

分 类 号：O62[理学—有机化学]