The Negishi reaction is a Pd(0)-catalyzed cross-coupling reaction of organozinc compounds and aryl or vinylic iodides, as in the example shown in Fig. P18.79.

(a) Outline a mechanism of this coupling reaction by showing the important catalytic intermediates.

(b) Show how the organozinc compound could be prepared from o-iodotoluene.

Transcribed Image Text:

O₂N- Figure P18.79 Br + CH3 ZnCl Pd(PPH3)4 ether O₂N- H₂C (78% yield) + BrZnCl