Iron-Catalyzed Synthesis of β-Chlorovinyl and α,β-Alkynyl Ketones from Terminal and Silylated Alkynes with Acid Chlorides - Gandeepan - 2012 - Advanced Synthesis & Catalysis - Wiley Online Library

Abstract
A simple efficient method for the iron(III)-catalyzed synthesis of substituted β-chlorovinyl ketones and α,β-alkynyl ketones from terminal and silyl-substituted alkynes with acid chlorides, respectively, is described. This method features easily available starting materials, a cheap and non-toxic catalyst, simple manipulation and mild reaction conditions. Evidence shows that the catalytic addition of the acid chloride to a terminal alkyne to give (Z)-β-chlorovinyl ketones favours a concerted pathway via a four-membered ring transition state between the two alkyne carbons and the carbon-chloride bond of the acid chloride.

1. Parthasarathy Gandeepan, 
2. Kanniyappan Parthasarathy, 
3. Tsu-Hui Su, 
4. Chien-Hong Cheng^* 

DOI: 10.1002/adsc.201100670