Enynes haloalkyne coupling

Using ( )-methylalkenylalanes 140, obtained by highly stereo- and regioselective Zr-catalyzed carboalumination of alkynes, the stereochemically defined enynes 141 can also by synthesized by Pd-catalyzed cross-coupling reactions with 1-haloalkynes [Eq. (47)] [68]. 

Enynes and arenynes are available from the Pd(Ph3P)4-catalyzed coupling of metalated alkynes (Mg, Al, 4,27 2n, 7f,28 Sn 29) with vinyl or aryl halides, triflates or phosphates (eq 8). Alternatively, 1-haloalkynes and metalated alkenes (B 4 orZn i7 ) can be utilized in similar procedures. 

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