Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent
Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent
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DOI：
10.3390/m976
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发表时间：
2018-01
期刊：
影响因子：
0.6
通讯作者：
Shotaro Izawa;H. Nakatsuji;Y. Tanabe
中科院分区：
文献类型：
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作者：
Shotaro Izawa;H. Nakatsuji;Y. Tanabe
以PhNMe2和AlCl3为催化剂，N-甲基-2-溴苯胺与氯甲酰亚硫氯(CCSC)进行环合反应，高产率地合成了N-甲基-2-溴-2(3H)-苯并噻唑-2-酮。在PdCl2(PPh3)2催化剂存在下，该溴代2(3 H)-苯并噻唑-2-酮与双(Pinacolato)二硼酮[(Pinacolato)2B2]发生宫仓-石山交叉偶联反应，合成了N-甲基-4-(Pin)B-2(3H)-苯并噻唑-2-酮(3)。得到的4-(Pin)B化合物被认为是Suzuki-Miyaura交叉偶联反应文库的新条目。
Cyclo-condensation of N-methyl-2-bromoaniline with chlorocarbonylsulfenyl chloride (CCSC) promoted by PhNMe2 and AlCl3, afforded N-methyl-2-bromo-2(3H)-benzothiazol-2-one in good yield. Miyaura–Ishiyama cross-coupling of this brominated 2(3H)-benzothiazol-2-one with bis(pinacolato)diborone [(pin)2B2] produced a novel N-methyl-4-(pin)B-2(3H)-benzothiazol-2-one (3) using (pin)2B2 in the presence of the PdCl2(PPh3)2 catalyst. The obtained 4-(pin)B compound is regarded as a new entry for the library of Suzuki–Miyaura cross-coupling reactions.