The reaction features combination of CH activation and ring opening of cyclopropanol was studied with the aid of DFT calculations. With the reaction of N-pyrimidylindoline and 1-benzylcyclopropanol as an example to accomplish the alkylation, we found the order of CH activation/ring opening is difficult to occur. Instead, the order of ring opening/CH activation is predicted to be more reasonable, which circumvents the N→Rh bond breaking. Two catalytic cycles were suggested. The first cycle relates to the catalytic oxidation of cyclopropanol by Cu(II) to generate an intermediate product, the vinyl ketone. The mechanism mainly involves prior ring opening of cyclopropanol and β-H elimination. The second cycle relates to the product formation from the resultant intermediate product, in which the CH activation of N-pyrimidylindoline, CC bond insertion of the intermediate product and protonation are included. The insights gained in this study are expected to be pertinent in other reaction systems involving combination of CH activation and ring opening.

借助DFT计算研究了C H活化和环丙醇开环的反应特征。以N-嘧啶基吲哚啉与1-苄基环丙醇的反应为例，完成烷基化反应，我们发现C H活化/开环的顺序很难发生。相反，开环顺序/ C预计H活化更为合理，这可以避免N→Rh键断裂。建议了两个催化循环。第一循环涉及通过Cu（II）催化氧化环丙醇以产生中间产物，乙烯基酮。该机理主要涉及环丙醇的事先开环和β-H的消除。第二个循环涉及由所得中间产物形成产物，其中包括N-嘧啶基二氢吲哚的CH活化，中间产物的CC键插入和质子化。预期在这项研究中获得的见解将与涉及C H活化和开环的其他反应系统有关。