Perfluoroalkynylzinc reagents

Perfluoroalkynylzinc reagents have been prepared by three methods ... 

Perfluoroalkynylzinc reagents do not generally undergo direct acylation or allylation. One exception, however, is reaction of bis(trifluoropropynyl)zinc with benzoyl chloride, without catalyst, to give the aroyltrifluoromethyl acetylene (equation 97)98. 

The perfluoroalkynylzinc reagents exhibit good thermal stability.18 For example, C4F9C=CZnX in DMF showed only a 4% loss of activity after 36 days at room temperature. Decomposition occurred upon heating to 100 °C. 

Like their vinyl counterparts, these perfluoroalkynylzinc reagents undergo Pd(PPh3)4 catalysed coupling with aryl iodides and vinyl iodides or bromides to afford the corresponding aryl alkynes17,20 and enynes20 (Equations 4.7 and 4.8). 

---