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Synfacts 2014; 10(2): 0185
DOI: 10.1055/s-0033-1340578
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

N–Bpin-Directed Borylation of (Hetero)Aryls

Contributor(s):
Paul Knochel
,
Thomas Klatt
Preshlock SM, Plattner DL, Maligres PE, Krska SW, * Maleczka Jr. RE, * Smith III MR. * Michigan State University, East Lansing and Merck Research Laboratories, Rahway, USA
A Traceless Directing Group for C–H Borylation.

Angew. Chem. Int. Ed. 2013;
52: 12915-12919
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Further Information

Publication History

Publication Date:
20 January 2014 (online)

 
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Key words

borylation - catalysis - nitrogen heterocycles

Significance

The authors report a regioselective pinacolatoboron (Bpin) functionalization of C–H bonds of nitrogen heterocycles and anilines. Traceless Bpin installation does not require the installation and removal of a directing group. This methodology clearly opens a new route to complex unsaturated boronic esters.


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Comment

For nitrogen heterocycles with less acidic NH groups, the addition of a tertiary amine is critical for successful borylation. For azaindoles, this preparation enables the formation of borylated heterocycles that are inaccessible with Boc-­directed methods.


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