Synthesis of Bis(indolyl)methanes Using Hyper-Cross-Linked Polyaromatic Spheres Decorated with Bromomethyl Groups as Efficient and Recyclable Catalysts

Highly uniform and hyper-cross-linked polyphenanthrene and polypyrene microspheres were synthesized by Friedel-Crafts bromomethylation of phenanthrene (Phn) and pyrene (Py) in the presence of zinc bromide as a catalyst, followed by self-polymerization of bromomethylated Phn and Py. The resultant 3-D carbon microspheres consisting of micro-, meso-, and macropores bear peripheral unreacted bromomethyl groups, which are directly utilized as catalysts to efficiently promote the electrophilic substitution reaction of indoles with aldehydes to yield a variety of bis(indolyl) methanes. The important features of this catalysis are easy catalyst synthesis, high product yields, environmental benignity, short reaction time, broad substrate scope, use of nontoxic solvents, and recyclability.