A Triphenylphosphine‐Based Microporous Polymer for a Wittig Reaction Cycle in the Solid State

Abstract

The Wittig reaction is a key step in industrial processes to synthesise large quantities of vitamin A and various other important chemicals that are used in daily life. This article presents a pathway to achieve the Wittig reaction in a solid network. A highly porous triphenylphosphine‐based polymer was applied as solid Wittig reagent which underwent, in a multi‐step cycle, in total six post‐synthetic modifications. This allowed to regenerate the solid Wittig reagent and reuse it for the same reaction cycle again. Of particular industrial relevance is that the newly developed material also enables a simple way of separating the product by filtration. Therefore, additional costly and difficult separation and purification steps are no longer needed.

Mechanosynthesis and Polymerization of Biosourced Styrene Derivatives Based on Building Blocks of Lignin

“…A Wittig reaction was then performed on the methylated substrates V1 , H1 , and S1 . Although the Wittig reaction generates a fair amount of waste, several studies try to tackle this issue by developing a catalytic Wittig reaction − or recycling the phosphine oxide byproduct . In our case, Wittig olefination was preferred over other strategies (e.g., Knoevenagel followed by decarboxylation) since it is robust, efficient, and compatible with mechanochemistry .…”

“…Although the Wittig reaction generates a fair amount of waste, several studies try to tackle this issue by developing a catalytic Wittig reaction 57−59 or recycling the phosphine oxide byproduct. 60 In our case, Wittig olefination was preferred over other strategies (e.g., Knoevenagel followed by decarboxylation) since it is robust, efficient, and compatible with mechanochemistry. 61 To improve the ecoefficiency of the procedure, solvent-free ball milling and conventional conditions in solution were compared.…”