Issue 24, 2016

PdII/CuBr2 catalysed keto α-Csp3–H benzoxylation of N,N-dialkylamides directed by o-hydroxy groups

Abstract

A hydroxy group directed keto α-Csp3–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.

Graphical abstract: PdII/CuBr2 catalysed keto α-Csp3–H benzoxylation of N,N-dialkylamides directed by o-hydroxy groups

Supplementary files

Article information

Article type
Communication
Submitted
31 Jan 2016
Accepted
16 Feb 2016
First published
16 Feb 2016

Chem. Commun., 2016,52, 4501-4504

PdII/CuBr2 catalysed keto α-Csp3–H benzoxylation of N,N-dialkylamides directed by o-hydroxy groups

S. K. Santra, A. Banerjee, S. Rajamanickam, N. Khatun and B. K. Patel, Chem. Commun., 2016, 52, 4501 DOI: 10.1039/C6CC00971A

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