What is it about?
1-Chlorovinyl p-tolyl sulfoxides are versatile intermediates that can be converted into alkynes via highly reactive magnesium alkylidene carbenoids. However, their preparation has required several separate synthetic steps. In this work, we developed a one-pot Horner–Wadsworth–Emmons reaction that converts readily available aldehydes and ketones directly into a wide range of 1-chlorovinyl p-tolyl sulfoxides. The products can be used without further modification as precursors to alkynes through the sulfoxide/magnesium exchange reaction followed by the Fritsch–Buttenberg–Wiechell rearrangement.
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Why is it important?
Efficient synthesis often depends on practical access to key synthetic intermediates. This one-pot method simplifies the preparation of 1-chlorovinyl p-tolyl sulfoxides, which serve as convenient precursors to highly reactive magnesium alkylidene carbenoids for alkyne synthesis and other useful transformations.
Perspectives
The one-pot strategy provides a practical platform for preparing structurally diverse 1-chlorovinyl p-tolyl sulfoxides from carbonyl compounds. The one-pot synthesis described here will make 1-chlorovinyl p-tolyl sulfoxides more readily accessible, facilitating further studies on their chemistry and expanding the applications of magnesium alkylidene carbenoids in organic synthesis.
Associate Professor Tsutomu Kimura
Read the Original
This page is a summary of: Efficient one-pot synthesis of 1-chlorovinyl p
-tolyl sulfoxides from aldehydes and ketones by the Horner-Wadsworth-Emmons reaction, Heteroatom Chemistry, September 2017, Wiley,
DOI: 10.1002/hc.21395.
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