A Surprising Substituent Effect Provides a Superior Boronic Acid Catalyst for Mild and Metal‐Free Direct Friedel–Crafts Alkylations and Prenylations of Neutral Arenes

Carolynne L. Ricardo, Xiaobin Mo, J. Adam McCubbin, Dennis G. Hall

doi:10.1002/chem.201500020

A Surprising Substituent Effect Provides a Superior Boronic Acid Catalyst for Mild and Metal‐Free Direct Friedel–Crafts Alkylations and Prenylations of Neutral Arenes

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書誌事項

公開日: 2015-02-10

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http://onlinelibrary.wiley.com/termsAndConditions#vor

DOI

10.1002/chem.201500020

公開者: Wiley

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<jats:title>Abstract</jats:title><jats:p>The development of more general and efficient catalytic processes for Friedel–Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5‐tetrafluorophenylboronic acid was identified as a potent air‐ and moisture‐tolerant metal‐free catalyst that significantly improves the scope of direct Friedel–Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.</jats:p>