Hydrosilylation reaction catalyst

Abstract

A hydrosilylation reaction catalyst prepared from: a prescribed transition metal compound such as iron pivalate, cobalt pivalate, iron acetate, cobalt acetate, or nickel acetate; a ligand comprising t-butylisocyanide or another isocyanide compound; and a borane compound, Grignard reagent, alkoxysilane, or other prescribed promoter makes it possible to promote a hydrosilylation reaction under moderate conditions, and has exceptional handling properties and storage stability.

Description

technical field [0001] The present invention relates to a hydrosilylation reaction catalyst, and more specifically, to a hydrosilylation reaction catalyst comprising a metal compound as a catalyst precursor, an isonitrile compound as a ligand component, and a cocatalyst. Background technique [0002] Addition reactions to compounds having carbon-carbon double bonds or carbon-carbon triple bonds The hydrosilylation reaction of Si—H functional compounds is a useful means for the synthesis of organosilicon compounds and is an industrially important synthesis reaction. [0003] Pt, Pd, and Rh compounds are known as catalysts for this hydrosilylation reaction, and among them, Pt compounds typified by Speier catalyst and Karstedt catalyst are most used. [0004] As a problem in the reaction using a Pt compound as a catalyst, a side reaction in which an internal rearrangement of an olefin occurs when a Si—H functional compound is added to a terminal olefin is mentioned. This syste...

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Problems solved by technology

[0013] However, the reaction using this complex has the following problems: the reactivity to internal olefins is low, the complex is synthesized using Na amalgam composed of water-restricted sodium and highly toxic mercury, and care must be taken in handling. The stability of the compound compound itself is low, and special equipment such as a glove box is required for handling. In addition, storage requires low temperature under an inert nitrogen atmosphere, etc.

[0015] A reaction example of an olefin and a trialkylsilane using a cobalt-carbonyl complex having a trialkylsilyl group as a substituent has also been reported (Non-Patent Document 15), but the yield is low and selectivity is lacking.

[0016] Although the reaction of alkenes and trialkylsilanes using cobalt-phosphite complexes having cyclopentadienyl as ligands has been reported (Non-Patent Document 16), the use of N-heterocyclic carbene as ligands The reaction of olefins and trihydrophenylsilanes of cobalt complexes (non-patent literature 17), but the stability of complex compounds is low, special equipment such as glove boxes are required in the process, and preservation needs to be in an inert nitrogen atmosphere and in low temperature

[0017] Although it has also been reported to use terpyridine, bisiminopyridine, bisiminoquinoline as examples of iron catalysts, cobalt catalysts, and nickel catalysts (patent documents 3 to 6) as ligands, it is different from the aforementioned non-patent documents 6 to 8. Similarly, there are the following problems: the synthesis of the catalyst precursor, or the synthesis from the precursor to the complex catalyst is not easy industrially, the stability of the complex compound itself is low, and special equipment is required for processing, etc.

However, in these patent documents, although hydrosilylation was carried out by several combinations, there is no description of the yield, etc., and it is not clear how far the reaction proceeds and the effect is unclear.

In addition, although ionic salts and hydride reducing agents are used as activators in all examples, almost all examples have no catalytic activity

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