Vicinal Dichlorination of o-Vinylbiphenyls and the Synthesis of 9-(Arylmethyl)fluorenes via Tandem Friedel–Crafts Alkylations
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Published:2019-05-28
Issue:13
Volume:51
Page:2648-2659
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ISSN:0039-7881
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Container-title:Synthesis
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language:en
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Short-container-title:Synthesis
Author:
Zhao Zhensheng,
Jameel Islam,
Murphy Graham K.ORCID
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.
Funder
Natural Sciences and Engineering Research Council of Canada
Publisher
Georg Thieme Verlag KG
Subject
Organic Chemistry,Catalysis