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Synfacts 2014; 10(9): 0963
DOI: 10.1055/s-0034-1378966
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereospecific Coupling of Aromatics with Secondary and Tertiary Boronates

Contributor(s):
Paul Knochel
,
Thomas Klatt
Bonet A, Odachowski M, Leonori D, Essafi S, Aggarwal VK * University of Bristol, UK
Enantiospecific sp2–sp3 Coupling of Secondary and Tertiary Boronic Esters.

Nature Chem. 2014;
6: 584-589
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Further Information

Publication History

Publication Date:
18 August 2014 (online)

 
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Key words

boron - aryllithium - cross-coupling

Significance

Aggarwal and co-workers report an effective, general method for coupling electron-rich (hetero)aromatics with enantioenriched secondary and tertiary boronic esters. The reaction involves the initial formation of a boronate complex followed by activation of the electron-rich ­aromatic by NBS, which triggers a stereospecific 1,2-migration and subsequent elimination–­rearomatization.


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Comment

The methodology uses simple, readily available reagents and proceeds without transition metals. Broad scope with respect to the boronic ester and the electron-rich aromatic was illustrated, and the reactions proceeded with complete stereospecificity.


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