含溴苯基取代卟啉与杂芳烃的直接催化芳基化反应
Direct catalytic arylation of heteroarenes with -bromophenyl-substituted porphyrins.
作者信息
Kiselev Alexei Nikolaevich, Grigorova Olga Konstantinovna, Averin Alexei Dmitrievich, Syrbu Sergei Aleksandrovich, Koifman Oskar Iosifovich, Beletskaya Irina Petrovna
机构信息
G. A. Krestov Institute of Solution Chemistry RAS, Akademicheskaya ul., Ivanovo, 153045, Russia.
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russia.
出版信息
Beilstein J Org Chem. 2017 Aug 3;13:1524-1532. doi: 10.3762/bjoc.13.152. eCollection 2017.
The arylation of mono-, di- and tetra--bromophenyl-substituted porphyrins with the heteroarenes containing "acidic" C-H bonds, such as benzoxazole, benzothiazole and -methylimidazole was studied in the presence of three alternative catalytic systems: Pd(dba)/DavePhos/CsCO, Pd(PPh)/PivOH/KCO and Pd(OAc)/Cu(OAc)/PPh/KCO. The first catalytic system was found to be successful in the reaction with benzoxazole, the second one was less efficient for our purpose, while the third system proved to be most versatile and afforded corresponding mono-, di-, tri- and even tetraarylated derivatives of porphyrins.
在三种不同的催化体系存在下，研究了单溴、二溴和四溴苯基取代卟啉与含有“酸性”C-H键的杂芳烃（如苯并恶唑、苯并噻唑和甲基咪唑）的芳基化反应。这三种催化体系分别是：Pd(dba)/DavePhos/CsCO、Pd(PPh)/PivOH/KCO和Pd(OAc)/Cu(OAc)/PPh/KCO。结果发现，第一种催化体系在与苯并恶唑的反应中取得成功，第二种体系对我们的目标反应效率较低，而第三种体系被证明是最通用的，能得到相应的卟啉单芳基化、二芳基化、三芳基化甚至四芳基化衍生物。
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