Sonogashira reaction synthetic utility

Z)-I-Bromo-4-trimethylsUyl-I-buten-3-yne (14). There have been a few papers reporting the synthesis of the Z isomer of 1. The most reasonable one appears to be that shown in eq 3. Since its cross-coupling and other synthetically useful reactions have not been adequately investigated, its synthetic utility remains largely unknown, although the Sonogashira alkynylation appears to proceed weU, as indicated in eq 3. ... 

Spiro-linked compounds containing heterocyclic units have been prepared for many apphcations. In general, there are two synthetic pathways to build up heterocyclic spiro compounds. On the one hand, cross-coupling reactions like the Negishi, Kharash, Stille, Suzuki, or Sonogashira coupling reaction can be utilized to connect the heterocychc subunit with the central spiro core [118]. On the other hand, the heterocycle can be built up from spiro precursors containing heteroatoms. 

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