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A Silica-Supported Titanium Catalyst for Heterogeneous Hydroamination and Multicomponent Coupling Reactions

A Silica-Supported Titanium Catalyst for Heterogeneous Hydroamination and Multicomponent Coupling Reactions

Kelly E Aldrich, Aaron L Odom

Dalton Trans. 2019 Aug 14;48(30):11352-11360.

PMID: 31281914

Abstract:

Highly dehydrated silica gel, SiO2700, gave a material with a total surface hydroxyl density of 0.31 ± 0.05 mmol g-1, 0.9 ± 0.1 Si-OH sites per nm2. Treatment of this material with Ti(NMe2)4 gave Ti(NMe2)3/SiO2700, which is 1.50% ± 0.07 Ti, where the titanium is bound to the surface, on average, through a single O-Si-Ti linkage. This material was tested for its properties as a catalyst for C-N bond forming reactions and was found to be a competent alkyne hydroamination and iminoamination catalyst. For iminoamination, which is the 3-component coupling of an alkyne, primary amine, and isonitrile, this heterogeneous catalyst was able to carry out some catalyses faster than previously reported homogeneous catalysts with lower catalyst loadings. The material is also a catalyst for the addition of aniline to dicyclohexylcarbodiimide to form a substituted guanidine. In addition, a known quinoline with biological activity was prepared using the heterogeneous catalyst in a one-pot procedure using half the catalyst loading of the previously reported synthesis.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LPLC81108	Silica gel 90 CN			Price

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