In the current research, a three component reaction [reported experimentally by Li et al. (Org Lett 19:1192–1195, 2017)] between the C₆₀ fullerene, indole and propargyl bromide is studied theoretically. According to the proposed mechanism in the experimental work, nucleophilic attack of indole anion (Ind⁻) to C₆₀ affords fulleroindole monoanion (FI) as an intermediate, which experiences another nucleophilic attack on certain primary organohalides to generate the corresponding 1,4-(3-indole)(organo)[60]fullerenes. To investigate the reaction from the mechanistic point of view, certain competition paths were designed between the starting materials in each step and some theoretical quantities were obtained and elucidated. In consistence with the experimental findings, the local Fukui as well as Parr functions reactivity indices confirmed the observed regioselectivity in the first step of the reaction. These local reactivity indices implied also that in the nucleophilic attack of FI on the organohalides, one of the ortho positions is more nucleophilically activated than para position. A PES analysis on the proposed reaction paths revealed a good agreement with the experimental findings. The electron transfer studies and the computation of molecular electrostatic potential (MEP) map of the transition states suggested that in addition to the steric repulsions, the electronic repulsions in the ortho positions determines the para-selectivity preference over the ortho ones.

在当前的研究中，三组分反应[Li等人的实验报告。（Org Lett 19：1192–1195，2017）]对C ₆₀富勒烯，吲哚和炔丙基溴之间的关系进行了理论研究。根据在实验工作提出的机制，吲哚阴离子的亲核攻击（工业^- ）至C _60所得到fulleroindole单价阴离子（FI）作为中间体，它对某些主要的有机卤化物经历另一次亲核攻击，生成相应的1,4-（3-吲哚）（有机）[60]富勒烯。为了从机理的角度研究反应，在每个步骤中在原料之间设计了一定的竞争路径，并获得了一些理论量并加以阐明。与实验结果一致，局部Fukui以及Parr功能反应性指数证实了在反应的第一步中观察到的区域选择性。这些地方的反应指数还暗示，在亲核攻击FI上的有机卤化物，在一个邻位更比亲核激活对位置。对提议的反应路径进行的PES分析显示与实验结果非常吻合。电子转移研究和分子静电势（MEP）的计算映射建议的过渡态的，除了立体排斥，在所述电子斥力邻的位置决定了对在-选择性偏好邻的。