Because indole compounds have many physiological activities, their synthesis has attracted wide attention, and many derivative reactions of indole have been studied in depth. In the indole molecule, the N atom provides two X electrons to participate in the covalent interaction of the whole ring system, which belongs to the super-two electron ring system. This ring system is conducive to the electrophilic substitution reaction, especially the pyrrole ring part of the electron cloud density is relatively high, so that Indole is prone to nucleophilic reaction. Friedel-Crafts alkylation is the most common and important derivative reaction. The introduced alkyl can carry other functional groups. It has been reported in the literature that the alkylation of indole has been studied for many years. Generally speaking, the heterocyclic part has been studied more, while the benzene part has been studied less 5. There are many inherent factors affecting the alkylation of indoles: the acidic proton and strong coordination of indoles make indoles easy to polymerize, the Lewis acid catalyst needs stoichiometry, low regioselectivity and stereoselectivity control, etc.
There are many ways to realize the alkylation of indole compounds. The main difference is that the types of electrophilic reagents involved in the reaction are different. Among them, 1,2-1 addition of indole to dimethyl compounds (including imines), Michael-type reaction between indole and electron-deficient olefin bonds, and ring opening reaction of high-tension heterocyclic compounds (ethylene oxide and cycloethylimine, etc.) represent the most useful ways to realize the Fourier alkylation of indole. Transition metal-catalyzed alkylation of indoles with allyl derivatives containing departing groups has also been successfully applied.
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