《Table 3 Substrate scope of complex Ni Cl2L4 (4) catalyzed the C—C coupling Reactions》

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《2-吡唑啉-9-芳基邻菲咯啉镍配合物催化芳基卤化物和格氏试剂偶联反应的研究（英文）》

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a.R and X mean substituents in aryl halides.The reactions were carried out using 1 mol%4，aryl halides 1.0 mmol，PhMgBr 1.2 mmol for 24 h at 20℃in 5 m L toluene；b.GC yield

With the optimized conditions in hand，the scope of aryl halides was investigated（Table 3）.For example，complex 4 acted as an efficient catalyst for the substrateof p-MeC6H4I，reaching 90%yield within 24 h at room temperature（Table 3，entry 6）.Under same conditions，when p-CF3C6H4I as a substrate gave excellent conversations（yield up to 98%，Table 3，entry 7）.On the same experimental conditions，complex 4 also applies to deactivated substrate such as 4-ioideanisol，but the yield of the corresponding product is a bit lower，reaching 63%yields for deactived aryl iodides over a period of 24 h（Table 3，entry 5）.Probably because of the nature of the substituents（electron-withdrawing or electron-donating substituents）in the aromatic substrates，which play a key role on the activation of C—I bboonnddss..UUnnffoorrttuunnaatteellyy，，wwhheenn ddeeaaccttiivvaatteedd ssuubbssttrraatteess 44--bromotoluene and 4-bromoanisole were involved，only moderate or trace amounts of products were observed.In expectation，due to low reactivity of aryl chlorides，nickel complexes are almost inefficient even for the coupling reaction of activated 4-chlorotoluene and PhMgBr.It is easily explain that C—Cl bond（Ph—X bond dissociation energies （BDEs）[34]:Cl，402 k J/mol；Br，339 kJ/mol；I，272 kJ/mol） much stronger.In addition，the steric hindrance of the substituent has little influence on the product yield in the C—C coupling reaction.