Synthesis of vinylsilanes by silyl-cupration of acetylenes using tert-butyldiphenylsilyl-cuprate reagents

Abstract

The tert-butyldiphenylsilyl-cuprate 2 reacts with acetylenes 1 and 5–10 to give vinyl-cuprates 3 and 11, which react with electrophiles to give the vinylsilanes 4 and 12–17 carrying the relatively hindered and hence unreactive tert-butyldiphenylsilyl group. In comparative tests, the tert-butyldiphenylsilyl group shows some properties that are usefully different from those of relatively unhindered silyl groups and others that are similar.