Conditions for hydrosilylation of end-functionalized alkenes using Karstedt's catalyst

CHED 366

Jacob D. Acton, jda2k@mtsu.edu, Jerry R. Oxsher, jro2d@mtsu.edu, and Andrienne C. Friedli. Department of Chemistry, Middle Tennessee State University, Box X076 MTSU, Murfreesboro, TN 37132
In our approach to highly sensitive biosensors, we require ultrathin films to bind silica surfaces to biomolecules. Ideal precursors to these films are end-functionalized-decyltrimethoxysilanes X-(CH2)10Si(OMe)3, where X includes: primary amines, aldehydes, and epoxides. Functionalized silanes with protecting groups: carbamates (protected amines), benzyl ethers (protected alcohols), and esters (protected acids) were also targeted. Unexpectedly, low conversion and long reaction times were observed in the hydrosilylation reaction of 10-amino-1-decene with trimethoxysilane using chloroplatinic acid as catalyst to produce 10-aminodecyl trimethoxysilane. Variation of reaction conditions, including the alternative Karstedt's catalyst, was investigated. For comparison, reactions of a variety of end-functionalized alkenes were carried out on a small scale in NMR tubes using ultrasound with or without heating in the presence of Karstedt's catalyst. Both heating and ultrasound (at lower temperatures) were found to improve yields and conversion times for hydrosilylation of amines.