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Synlett 2013; 24(3): 269-275
DOI: 10.1055/s-0032-1317744
DOI: 10.1055/s-0032-1317744
synpacts
Copper-Catalyzed Electrophilic Amination of Organoboron Compounds
Further Information
Publication History
Received: 07 October 2012
Accepted after revision: 13 November 2012
Publication Date:
12 December 2012 (online)
Abstract
A new procedure for direct transformation of alkenes to tertiary alkylamines based on hydroboration and copper-catalyzed amination of alkylboranes is described. The new method is presented in a broader context provided by a brief analysis of various approaches to the formation of anti-Markovnikov hydroamination products. A short discussion of the reaction development, scope, and the mechanism are also provided. Finally, the extension of this methodology to the preparation of hindered anilines from aryl boronic esters is presented.
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For reviews, see:
Selected examples of intramolecular hydroamination using complexes of group IV metals and lanthanides:
Selected examples of intramolecular hydroamination using complexes of late transition metals:
The synthesis of dimethylborane is fully described in the following two papers:
Potassium organotrifluoroborates bearing amine functionality have been used in palladium-catalyzed Suzuki–Miyaura cross-couplings with aryl halides and mesylates for the preparation of anilines, amides, and benzylamines. Please see:
Selected examples:
For reviews of electrophilic amination, see:
For other examples of electrophilic amination used to prepare aniline derivatives, see: