Pd(II)-catalyzed ortho-C-H oxidation of arylacetic acid derivatives: synthesis of benzofuranones

Raja K Rit; M Ramu Yadav; Akhila K Sahoo

doi:10.1021/ol403699d

Pd(II)-catalyzed ortho-C-H oxidation of arylacetic acid derivatives: synthesis of benzofuranones

Org Lett. 2014 Feb 7;16(3):968-71. doi: 10.1021/ol403699d. Epub 2014 Jan 30.

Authors

Raja K Rit¹, M Ramu Yadav, Akhila K Sahoo

Affiliation

¹ School of Chemistry, University of Hyderabad , Hyderabad-500046, India.

PMID: 24479983
DOI: 10.1021/ol403699d

Abstract

Pd(II)-catalyzed ortho-C-H acetoxylation of arylacetic acid derivatives is demonstrated with the aid of a novel S-methyl-S-2-pyridylsulfoximine (MPyS) directing group (DG). The α-mono- and α-unsubstituted arylacetic acid derivatives were readily employed in the ortho-C-H acetoxylations. The oxidation products are hydrolyzed, and the MPyS-DG is easily recovered, providing ready access to o-hydroxyarylacetic acids. 3-Mono- and 3-unsubstituted benzofuranones are synthesized from o-hydroxyarylacetic acids.