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Issue 33, 2012
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1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide

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Abstract

A series of 2-(picolyl)borane molecules were synthesized as products of the reaction between 2-(picolyl)lithium and R2BOMe (R = ethyl, 9-BBN, phenyl, 9-borafluorenyl). The 2-(picolyl)boranes were dimeric; whereas, monomers coordinated to LiOMe could be isolated when the synthesis was carried out in the presence of TMEDA and THF. The 2-(picolyl)boranes undergo reaction with nitriles, ketones, aldehydes, and amides with apparent 1,2-addition of the B–C(picolyl) bond to the unsaturated bond. Theoretical models reveal the presence of a donor orbital on the 2-(picolyl)borane with significant electron density at the benzylic carbon that we conclude was involved in nucleophilic attack on the electrophilic center of unsaturated organic functional groups.

Graphical abstract: 1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide

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Publication details

The article was received on 09 Mar 2012, accepted on 21 Jun 2012 and first published on 21 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25518A
Citation: Org. Biomol. Chem., 2012,10, 6656-6664
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    1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide

    J. Son and J. D. Hoefelmeyer, Org. Biomol. Chem., 2012, 10, 6656
    DOI: 10.1039/C2OB25518A

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