Abstract
Functionalized siloxanes are one of the most important classes of organosilicon compounds, thus the enhancement of current methods of its synthesis is an important issue. Herein, we present the selective and highly effective reaction between 1,1,3,3-tetramethyldisiloxane (TMDSO) and 1-octene (1-oct), using SILP (supported ionic liquid phase) materials containing a rhodium catalyst immobilized in three phosphonium ionic liquids (ILs) differing in the structure of cation. Studies have shown high potential for using SILP materials as catalysts due to their high catalytic activity and selectivity, easy separation process, and the possibility of reusing the catalyst in subsequent reaction cycles without adding a new portion of the catalyst. Using the most active SILP material SiO2/[P66614][NTf2]/[{Rh(μ-OSiMe3)(cod)}2] allows for reuse of the catalyst at least 50 times in an efficient and highly selective monofunctionalization of TMDSO.
Highlights
Functionalized organosilicon compounds, due to their unique properties, have generated much attention in a variety of organic processes [1,2,3]
We have successfully developed a strategy for high-yield and selective synthesis of monofunctionalized TMDSO derivatives while performing the reaction in a biphasic system, where the catalyst is immobilized in the ionic liquid phase [29]
Over 10 h), (iii) rhodium catalysts immobilized in ionic liquid are very efficient in the hydrosilylation reaction of 1-octene and TMDSO, and (iv) the high catalytic activity when using SILP materials with these ionic liquids
Summary
Functionalized organosilicon compounds, due to their unique properties, have generated much attention in a variety of organic processes [1,2,3]. Taking into account the importance of these compounds in industry, new methods of synthesis are being sought. One of the most interesting examples of these compounds is 1,1,3,3-tetramethyldisiloxane (TMDSO), which can be used in such applications as preparation of functionalizing agents of fluorinated polyethers [4], polysiloxane ingredients for heat conductible silicone compositions [5], and surfactants for the production of skincare cosmetics [6]. The conventional methods for obtaining unsymmetrical silicon-based compounds involve the condensation reactions and co-hydrolysis reactions of two silanols—chlorosilanes and alkoxysilanes [7]. The hydrosilylation reaction seems to be the most convenient procedure for the synthesis of new organosilicon derivatives [8,9,10].
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