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Synfacts 2015; 11(11): 1193
DOI: 10.1055/s-0035-1560742
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Regioselective Aromatic C–H Borylation

Contributor(s):
Paul Knochel
,
Diana Haas
Kuninobu Y, * Ida H, Nishi M, Kanai M. * The University of Tokyo and ERATO, Tokyo, Japan
A meta-Selective C–H Borylation Directed by a Secondary Interaction between Ligand and Substrate.

Nature Chem. 2015;
7: 712-717
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Further Information

Publication History

Publication Date:
19 October 2015 (online)

 
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Key words

borylation - regioselectivity - iridium

Significance

Kanai, Kuninobu, and co-workers report a meta-selective C(sp2)–H borylation directed by a hydrogen-bonding secondary interaction between the substrate and the ligand. The reaction shows wide substrate scope and high functional group tolerance. Moreover, the employed ligand L is easily accessible.


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Comment

The secondary interaction between the urea-derived ligand L and a hydrogen-bond acceptor in the substrate places the iridium catalyst in close proximity to the meta-C–H bond and thus controls the regioselectivity in this protocol.


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