Co-Mediated Synthesis of Alkenyl- and Alkynyl Silanes from Alkyl Halides

Significance

The authors describe a novel interesting protocol for the synthesis of TMS-substituted alkynes and alkenes by the cross-coupling of primary and secondary alkyl bromides and iodides with the corresponding Grignard reagents. A number of functionalized alkyl halides were shown to react successfully. The reaction is an alternative to the, often problematic, alkylation of acetylenes and represents a practical method for the preparation of terminal TMS-alkenes. Tandem radical cyclization-cross-coupling reactions can be performed in good yields for the appropriate substrates.