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

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

Chemistry. 2015 Mar 9;21(11):4218-23.

PMID: 25678266

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP179923321	2,3,4,5-Tetrafluorophenylboronic acid		179923-32-1	Price

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