Issue 47, 2016

Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids

Abstract

A novel cobalt-promoted arylation of aryl C–H bonds with arylboronic acids has been realized by using 8-aminoquinoline as the directing group. The reaction tolerated a wide variety of functional groups and diversely substituted ortho-arylated benzamides were efficiently synthesized in good to excellent yields. Even though a catalytic amount of a Co-salt was enough to effect the transformation, better yields were obtained with a stoichiometric amount of the Co-salt. A notable feature of this newly developed protocol is that acrylamides, which cannot be arylated using copper salts as the promoter, can also be efficiently arylated. In addition, the stereochemistry of these arylation products can be largely retained under the standard conditions.

Graphical abstract: Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids

Supplementary files

Article information

Article type
Communication
Submitted
12 Oct 2016
Accepted
07 Nov 2016
First published
08 Nov 2016

Org. Biomol. Chem., 2016,14, 11070-11075

Cobalt-promoted selective arylation of benzamides and acrylamides with arylboronic acids

L. Hu, Q. Gui, X. Chen, Z. Tan and G. Zhu, Org. Biomol. Chem., 2016, 14, 11070 DOI: 10.1039/C6OB02224C

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