Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
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DOI：
10.1021/acs.joc.7b01525
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发表时间：
2017-09-15
影响因子：
3.6
通讯作者：
Kondo, Yoshinori
中科院分区：
文献类型：
--
作者：
Nozawa-Kumada, Kanako;Osawa, Sayuri;Kondo, Yoshinori
开发了一种使用三氟甲基三甲基硅烷（CF3SiMe3，鲁珀特-普拉卡什试剂）和催化量的氟化物对芳香族 C-H 键进行去质子硅烷化的方法。在此反应中，CF3SiMe3 被认为充当碱和硅亲电子试剂。该过程对杂芳烃和苯上的各种官能团具有高度耐受性。此外，该方法还可用于合成含有三甲基甲硅烷基的TAC-101类似物，这是一种生物活性合成类视黄醇，对视黄酸受体α（RAR-α）结合具有选择性亲和力。我们还报告了硅烷化产物进一步转化为有用的衍生物。
A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor alpha (RAR-alpha) binding. We also report further transformations of the silylated products into useful derivatives.