Direct Access to Fluorene by Successive C–O/C–H Bond Activations of 2-Phenylbenzyl Ester
Direct Access to Fluorene by Successive C–O/C–H Bond Activations of 2-Phenylbenzyl Ester
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DOI：
10.1021/om5001869
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发表时间：
2014-04
期刊：
影响因子：
2.8
通讯作者：
M. Hirano;Sosuke Kawazu;Nobuyuki Komine
中科院分区：
文献类型：
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作者：
M. Hirano;Sosuke Kawazu;Nobuyuki Komine
以Pd(OAc)2/PPh3为催化剂，通过连续的C-O和C-H键断裂反应，以97%的产率实现了2-苯基苄基三氟乙酸酯催化合成荧烯。该反应包括酯的氧化加成得到(羧基)(2-苯基苄基)钯(II)物种，以及通过内部亲电取代机理从2-苯基苄基上裂解的羧基上的去质子化。
Catalytic formation of fluorene has been achieved from 2-phenylbenzyl trifluoroacetate via successive C–O and C–H bond cleavage reactions by Pd(OAc)2/PPh3 in 97% yield. This reaction involves the oxidative addition of ester to give (carboxylato)(2-phenylbenzyl)palladium(II) species and deprotonation from the 2-phenylbenzyl group by the cleaved carboxylato group via an internal electrophilic substitution mechanism.