☆ 4.6 Article

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

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Journal

CHEMISTRY-A EUROPEAN JOURNAL

Volume 21, Issue 11, Pages 4218-4223

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/chem.201500020

Keywords

arenes; boronic acid; heterogeneous catalysis; Friedel-Crafts alkylation; fluoride substituent

Categories

Chemistry, Multidisciplinary

Funding

Natural Science and Engineering Research Council of Canada
University of Alberta
University of Winnipeg
American Chemical Society Petroleum Research Fund [52231-URI]
Alberta Innovates [201400346] Funding Source: researchfish

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Abstract

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.

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