Hydrosilylation reaction catalyst

Abstract

A hydrosilylation reaction catalyst prepared from: a catalyst precursor comprising a transition metal compound, excluding platinum, belonging to group 8-10 of the periodic table, e.g., iron acetate, cobalt acetate, nickel acetate, etc; and a ligand comprising a carbine compound such as 1,3-dimesitylimidazol-2-ylidene, etc.. The hydrosilylation reaction catalyst has excellent handling and storage properties. As a result of using this catalyst, a hydrosilylation reaction can be promoted under gentle conditions.

Description

technical field [0001] The present invention relates to a hydrosilylation catalyst, and more specifically, to a hydrosilylation catalyst comprising a metal compound as a catalyst precursor and a carbene compound as a ligand component. Background technique [0002] A hydrosilylation reaction in which an Si-H functional compound is added to a compound having a carbon-carbon double bond or a carbon-carbon triple bond is a useful means for synthesizing organosilicon compounds and is an industrially important synthesis reaction. [0003] As catalysts for this hydrosilylation reaction, Pt, Pd, and Rh compounds are known, and among them, Pt compounds represented by Speier catalyst and Karstedt catalyst are most widely used. [0004] As a problem in the reaction using a Pt compound as a catalyst, a side reaction in which an olefin internal rearrangement occurs when a Si—H functional compound is added to a terminal olefin is mentioned. Since this system does not show addition reacti...

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Problems solved by technology

[0013] However, in the reaction using this complex, there are problems in that the reactivity to internal olefins is low, and Namercury, which is composed of water-repellent sodium and highly toxic mercury, is used for complex synthesis, and requires attention in handling. Qi (or use water-restricted NaBEt 3 H), the stability of the coordination compound itself is low, and special equipment such as glove boxes are required for processing. In addition, it must be stored under an inert gas nitrogen atmosphere and at low temperature

[0015] An example of the reaction of an alkene with 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 also lacking

[0016] The reaction of olefins and trialkylsilanes by using cobalt-phosphite complexes having cyclopentadienyl as ligands has been reported (Non-Patent Document 16), using N-heterocyclic carbene as ligands. The reaction of olefins and trihydrophenylsilanes of cobalt complexes (non-patent literature 17), but the stability of coordination compounds is low, and special equipment such as glove boxes are required for handling, and preservation needs to be carried out under an inert gas atmosphere and low temperature

[0017] Examples of iron, cobalt, and nickel catalysts in which the ligand is terpyridine, bisiminopyridine, or bisiminoquinoline have also been reported (Patent Documents 3 to 6), but the same as the above-mentioned Non-Patent Documents 6 to 8 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 coordination compound itself is low, and special equipment is required for handling

[0048] In addition, all of the examples shown in these patent documents 21 to 26 used ionic salts or hydride reducing agents as activators, but almost all of the examples did not show catalytic activity.

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