Aiming at the problems of high catalyst cost and harsh reaction conditions in the traditional C(sp3)—H bond functionalization reaction of quinoline derivatives,this study is performed upon the functionalization reaction between amino acid-mediated benzyl C(sp3)—H bond of 2-methylquinoline (2-MQ) and N-benzylidene-4-methylbenzenesulfonamide (compound Ⅰ).The yield of 4-methyl-N-[1-phenyl-2-(quinoline-2-yl)ethyl]benzenesulfonamide (compound Ⅱ) reaches 71.1% after 24 h under the conditions that the dosages of 2-MQ,compound Ⅰ,L-leucine and water are 0.42 mmol,0.3 mmol,0.2 mmol,2 mL,respectively,and reaction temperature is 90℃.It is indicated by the calculation that the activation energy of the reaction after adding L-leucine is 23.89 kJ/mol,which is significantly lower than that (88.57 kJ/mol) without adding L-leucine,representing that the addition of L-leucine can reduce the activation energy barrier of the reaction effectively and make the reaction occur more easily.It is speculated that L-leucine involves in the activation of the methyl C(sp3)—H bond in 2-MQ and the imino group in compound Ⅰ,which promotes the formation of enamine intermediate,and stimulate its nucleophilic attack on imine groups.
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