三氟甲基三烷基硅烷和氟化物协同促进的芳基 C-H 键去质子化硅烷化反应。
Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride.
机构信息
Graduate School of Pharmaceutical Sciences, Tohoku University , 6-3, Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
Normandie Univ , UNIROUEN, COBRA, INSA Rouen, CNRS, COBRA, 76000 Rouen, France.
出版信息
J Org Chem. 2017 Sep 15;82(18):9487-9496. doi: 10.1021/acs.joc.7b01525. Epub 2017 Aug 28.
A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CFSiMe, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CFSiMe 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 α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.
一种使用三氟甲基三甲基硅烷（CF3SiMe3，Ruppert-Prakash 试剂）和催化量的氟化物对芳族 C-H 键进行脱质子甲硅烷基化的方法已经开发出来。在该反应中，CF3SiMe3 被认为是一种碱和硅亲电试剂。该过程对杂芳环和苯上的各种官能团具有很高的容忍度。此外，该方法可用于合成 TAC-101 的含三甲基硅基的类似物，TAC-101 是一种具有选择性亲和力的生物活性合成维甲酸，可与视黄酸受体α（RAR-α）结合。我们还报告了将甲硅烷基化产物进一步转化为有用的衍生物。
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