Anna Szymańska*, Michał Dutkiewicz and Hieronim Maciejewski,
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Thiol-isocyanate Click Reaction for Rapid and Efficient Generation of a Library of Organofunctional Silanes
Herein, we report a simple, very fast, and efficient method for the synthesis of a library of organofunctional alkoxysilanes based on an amine-catalyzed thiol-isocyanate click reaction. At first, systematic studies were carried out to select the most active catalyst and its concentration for the model reaction involving 3-isocyanatopropyltriethoxysilane (ICPTES) and 1-octanethiol. Six tertiary amines were studied using an in situ FT-IR technique. After an effective catalytic system was selected, a set of alkoxysilanes containing various functional groups were synthesized. In addition, new thiols and thioacetates (sequentially reduced to thiols) were obtained as a result of the thiol–ene reaction. Two synthetic routes were applied to obtain alkoxysilanes, the reaction between ICPTES and functional-group-containing thiols or between 3-mercaptopropyltriethoxysilane (MPTES) and functional-group-containing isocyanates. The developed procedure permitted the synthesis of 13 new organosilicon compounds. The silanes obtained contain various functional groups, i.e. long alkyl or fluoroalkyl chain, phenyl, trisiloxane, naphthyl, trisilylamine, or polyether.
期刊介绍:
Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.