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

作者：Ricardo Carolynne L; Mo Xiaobin; McCubbin J Adam; Hall Dennis G^*

来源：Chemistry - A European Journal, 2015, 21(11): 4218-4223.

DOI：10.1002/chem.201500020

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

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.

• 出版日期2015-3-9