One-Pot Combination of the Wittig Olefination with Bromination and Oxidation Reactions

Abstract

A simple one-pot process for in situ bromination of (ethoxycarbonylmethylene)-triphenylphosphorane 1 was carried out. This was followed by oxidation of alcohol using SO₃. Pyridine complex as a mild oxidant and in situ trapping of the aldehyde. This process constitutes a stereoselective one-pot procedure for the preparation of Z-configured α-bromo-α, β-unsaturated esters in good yield.

GRAPHICAL ABSTRACT

Keywords:

• Halogenation
• olefination
• one-pot synthesis
• oxidation

ACKNOWLEDGMENT

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through Research Group Project No. RGP-VPP-128.

Notes

^a Yields were based on alcohols. ^b This ratio was determined by ¹H NMR spectroscopy.