A NOVEL COPPER-CATALYZED C-C BOND CLEAVAGE OF ARYL (HETEROARYL) ALKYL KETONES FOR C-N BOND FORMATION

Maryam Sadat Hosseini-Zare, Mehdi Bakavoli*, Hossein Eshghi and Ali Shiri

ABSTRACT

A direct generation of amide from aryl (heteroaryl) alkyl ketones has been accomplished via copper(II) catalyzed C-C bond cleavage in the presence of diisopropylamine at moderate temperature. The transformation steps for amide formation comprise catalytic generation of α-bromo carbonyl species followed by nucleophilic displacement of bromide with sodium azide in the presence of diisopropylamine. The final step involves the formation of imine by heating in situ followed by hydrolysis to give the related amide.

Keywords: ketones, cleavage reaction, amide, cupper catalist.