Acyl hydrazides as acyl donors for the synthesis of diaryl and aryl alkyl ketones

Ahmed R Akhbar,Stephen Caddick,Lyn Powell,Richard J Fitzmaurice,Vijay Chudasama

doi:10.1039/c3cc47967f

Abstract

In this communication we describe a novel strategy for the formation of valuable diaryl and aryl alkyl ketones from acyl hydrazides. A wide variety of ketones are prepared and the mild reaction conditions allow for the use of a range of functionalities, especially in the synthesis of diaryl ketones.

Highlights

In this communication we describe a novel strategy for the formation of valuable diaryl and aryl alkyl ketones from acyl hydrazides
A wide variety of ketones are prepared and the mild reaction conditions allow for the use of a range of functionalities, especially in the synthesis of diaryl ketones
Owing to the mildness of the reaction conditions required for effective conversion, we appraised the use of acyl hydrazides bearing functionalities that were not tolerant of Weinreb amide ketone synthesis conditions, i.e. nitro- and cyanogroups (Table 2, entries 10 and 11)

Summary

Introduction

In this communication we describe a novel strategy for the formation of valuable diaryl and aryl alkyl ketones from acyl hydrazides. This afforded increasingly higher conversion of acyl hydrazide 1a (i.e. from 80% to 100%) with an excellent yield of ketone, 78%, being observed with 2.5 equivalents of 2a (Table 1, entry 10).

Results

Conclusion