Pd(II)/CuBr2 catalysed keto α-C(sp3)-H benzoxylation of N,N-dialkylamides directed by o-hydroxy groups

Sourav Kumar Santra; Arghya Banerjee; Suresh Rajamanickam; Nilufa Khatun; Bhisma K Patel

doi:10.1039/c6cc00971a

Pd(II)/CuBr2 catalysed keto α-C(sp3)-H benzoxylation of N,N-dialkylamides directed by o-hydroxy groups

Chem Commun (Camb). 2016 Mar 25;52(24):4501-4. doi: 10.1039/c6cc00971a.

Authors

Sourav Kumar Santra¹, Arghya Banerjee¹, Suresh Rajamanickam¹, Nilufa Khatun¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati, 781 039, Assam, India. patel@iitg.ernet.in.

PMID: 26931492
DOI: 10.1039/c6cc00971a

Abstract

A hydroxy group directed keto α-C(sp3)-H benzoxylation of amides, including N,N-dialkylamides and cyclic amides, has been accomplished involving ortho-hydroxy substrates possessing either an aldehydic or a keto methyl (-COCH3) group with a Pd(II)/CuBr2 catalytic combination. The carboxy group obtained via the in situ oxidation of -CHO or -COCH3 groups of ortho-hydroxy substrates then undergoes a cross-dehydrogenative coupling (CDC) with amides to furnish an α-benzoxylation product with concurrent aromatic ring bromination.