title: A surprising substituent effect provides a superior boronic acid catalyst for mild and metal-free direct Friedel-Crafts alkylations and prenylations of neutral arenes.
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.
authors: Department of Chemistry, University of Alberta, 4-010 Centennial Centre for Interdisciplinary Science, Edmonton, Alberta, T6G 2G2 (Canada).
authors: Carolynne L
authors: CL
authors: Ricardo
authors: Xiaobin
authors: X
authors: Mo
authors: J Adam
authors: JA
authors: McCubbin
authors: Dennis G
authors: DG
authors: Hall
mesh_terms: D000478:Alkylation; D001897:Boronic Acids / Q000378:metabolism*; D002384:Catalysis; D015394:Molecular Structure; D054876:Prenylation
chemical_list: D001897:Boronic Acids
keywords: Friedel-Crafts alkylation; arenes; boronic acid; fluoride substituent; heterogeneous catalysis