BF3.2CF3CH2OH (BF3.2TFE), an efficient superacidic catalyst for some organic synthetic transformations

G K Surya Prakash; Thomas Mathew; Eric R Marinez; Pierre M Esteves; Golam Rasul; George A Olah

doi:10.1021/jo0604181

BF3.2CF3CH2OH (BF3.2TFE), an efficient superacidic catalyst for some organic synthetic transformations

J Org Chem. 2006 May 12;71(10):3952-8. doi: 10.1021/jo0604181.

Authors

G K Surya Prakash¹, Thomas Mathew, Eric R Marinez, Pierre M Esteves, Golam Rasul, George A Olah

Affiliation

¹ Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, 837 Bloom Walk, Los Angeles, California 90089-1661, USA. [email protected]

PMID: 16674072
DOI: 10.1021/jo0604181

Abstract

BF3.2CF3CH2OH complex was found to be a very effective superacidic catalyst comparable in acid strength to at least that of 100% anhydrous sulfuric acid for various acid-catalyzed organic transformations such as isomerizations, rearrangements, ionic hydrogenation of various ketones, and aromatics with triethylsilane and nitration of aromatics with metal nitrate. Studies of the pivalaldehyde-methyl isopropyl ketone rearrangement and the benzopinacol to phenanthrene transformation suggest that the complex has an acidity comparable to that of 100% anhydrous sulfuric acid. The structure and properties of the 1:2 boron trifluoride-trifluoroethanol complex have been further studied using NMR (1H, 13C, 19F, 11B) and DFT calculations at the B3LYP/6-311++G//B3LYP/6-31G level.