Katsukiyo Miura, K. Oshima, K. Utimoto
Aug 1, 1993
Citations
0
Influential Citations
31
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Triethylborane induced radical addition of various organosilanes (R3SiH) to acetylenes has been studied. Among them, tris(trimethylsilyl)silane (TTMSS) proved to be the best reagent for the hydrosilylation of acetylenic compounds in terms of yield and stereoselectivity. For instance, reaction of 1-dodecyne with TTMSS at room temperature for 3 h under Et3B catalyst provided (Z)-1-tris(trimethylsilyl)silyl-1-dodecene selectively in 98% yield. The stereochemical course of reduction of alkenyl iodides with TTMSS–Et3B or n-Bu3SnH–Et3B has been examined. Treatment of 1-dimethylphenylsilyl-2-iodo-1-dodecene with TTMSS–Et3B at room temperature afforded (Z)-1-dimethylphenylsilyl-1-dodecene selectively (Z/E > 30/1). On the other hand, treatment with n-Bu3SnH-Et3B gave (E)-1-dimethylphenylsilyl-1-dodecene exclusively.