The Negishi reaction is a Pd(0)-catalyzed cross-coupling reaction of organozinc

Chapter 18, Problem 18.79

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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 on p. 942. (Ei-ichi Negishi, a Professor at Purdue University, shared the 2010 Nobel Prize with Suzuki and Heck for his research into cross-coupling reactions.) (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. (Hint: See Eq. 18.50, p. 905.)

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