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. 2016 Oct 5;138(39):12775-12778.
doi: 10.1021/jacs.6b08478. Epub 2016 Sep 26.

Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

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Catalytic C-H Arylation of Aliphatic Aldehydes Enabled by a Transient Ligand

Ke Yang et al. J Am Chem Soc. .

Abstract

The direct arylation of aliphatic aldehydes has been established via Pd-catalyzed sp3 C-H bond functionalization in the presence of 3-aminopropanoic acids as transient directing groups. The reaction showed excellent functional group compatibility and chemoselectivity in which a predominant preference for functionalizing unactivated β-C-H bonds of methyl groups over others was achieved. In addition, C-H bonds of unactivated secondary sp3 carbons can also be functionalized. The extreme popularity and importance of aliphatic aldehydes would result in broad applications of this novel method in organic chemistry and medicinal sciences.

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