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. 2017 Feb 17;82(4):1931-1935.
doi: 10.1021/acs.joc.6b02677. Epub 2017 Jan 27.

"Naked" Lithium Cation: Strongly Activated Metal Cations Facilitated by Carborane Anions

Yu Kitazawa  1 , Ryo Takita  2 , Kengo Yoshida  2 , Atsuya Muranaka  2 , Seijiro Matsubara  3 , Masanobu Uchiyama  1   2
Affiliations

"Naked" Lithium Cation: Strongly Activated Metal Cations Facilitated by Carborane Anions

Yu Kitazawa et al. J Org Chem. .

Abstract

Experimental and spectroscopic studies revealed unprecedented reactivity of a "naked" lithium cation with very weakly coordinating anions, including carborane anions. The superactivated lithium cation has greatly enhanced Lewis acidic character and mediates various organic reactions such as carbonyl-ene reaction, NBS-bromination of unactivated aromatics, and Friedel-Crafts alkylation, which are not promoted by conventional lithium salts. Chemical robustness of the counteranion also plays an important role in the chemistry of the strongly activated lithium cation.

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