Abstract
Reacting ortho-vinylbiphenyls with (dichloroiodo)benzene (PhICl2) gives vicinal dichlorides, rapidly, and in excellent yield at room temperature. Treating the vic-dichlorides with 50 mol% AlCl3 in the presence of arene nucleophiles results in sequential intramolecular and intermolecular Friedel–Crafts alkylations to generate 9-(arylmethyl)fluorene derivatives. The dichlorination and alkylation reactions are operationally simple and tolerant of a variety of functional groups and substitution patterns, and give the products in moderate to excellent yield.
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