Vicinal Dichlorination of o-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl)fluorenes via Tandem Friedel–Crafts Alkylations

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.

Key words

fluorene - 1-aryl-1,2-dichloroethane - chlorination - hypervalent iodine - Friedel–Crafts

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