Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Direct Nucleophilic Substitution Reaction of Cage B−H Bonds by Grignard Reagents: A Route to Regioselective B4-Alkylation of o-Carboranes

Direct Nucleophilic Substitution Reaction of Cage B−H Bonds by Grignard Reagents: A Route to Regioselective B4-Alkylation of o-Carboranes
Cen Tang, Zuowei Xie, Jiji Zhang
Direct nucleophilic substitution reaction of cage B−H bonds of o-carboranes by Grignard reagents in the absence of any transition metals has been achieved for the first time, and leads to the regioselective synthesis of a series of 4-alkyl-1,2-diaryl-o-carboranes in very high yields. The presence of two electron-withdrawing aryl groups on the cage carbon atoms is crucial to realizing the reaction. The regioselectivity is controlled by both electronic and steric factors. This work represents a new strategy for the development of methods for carborane functionalization. Rattled cage: The title reaction proceeds in the absence of transition metals and leads to 4-alkyl-1,2-diaryl-o-carboranes in high yields. The presence of two electron-withdrawing aryl groups on the cage carbon atoms is crucial for the reaction, and the regioselectivity is controlled by both electronic and steric factors.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702347

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