α-CH acidity of alkyl-B(C6F5)2 compounds - the role of stabilized borata-alkene formation in frustrated Lewis pair chemistry.

Abstract

Alkyl-B(C6F5)2 boranes are markedly α-CH-acidic. Using DFT we have calculated the pKa-values of a series of examples. Typically, (C6F5)2B-CH3 [pKa (calcd) = 18.3 in DMSO, 16.2 in dichloromethane] is almost as CH-acidic as cyclopentadiene. However, this α-CH-B(C6F5)2 acidity is in most cases not sufficient to allow for internal proton transfer in vicinal… (More)
DOI: 10.1039/c4sc01711k

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