Phenylpalladium iodide complex

Sy 1 -phenylethyltrifluorosilane 439 1-phenylethylzinc chloride 27, 29 1 -phenyl-3-methyl-1,2-butadiene 475 (1Z,3E)-1-phenyl-1,3-octadiene, synthesis 84-5 phenylpalladium iodide complex 137 l-phenylpent-4-en-l-yne 196-7 (Z)-phenyl-substituted dendralene 117 ( -(-)-1 -phenyl-1 -trifluoroacetoxy-2-propyne 475 l-phenyl-4-triinethylsilyl but-2-ene 351... 

Organic compounds M—R and hydrides M—H of main group metals such as Mg, Zn, B, Al, Sn, SI, and Hg react with A—Pd—X complexes formed by oxidative addition, and an organic group or hydride is transferred to Pd by exchange reaction of X with R or H. In other words, the alkylation of Pd takes place (eq. 9). A driving force of the reaction, which is called transmetallation, is ascribed to the difference in the electronegativities of two metals. A typical example is the phenylation of phenylpalladium iodide with phenyltributyltin to form diphenylpalladium (16). 

Among many substrates used for Pd(0)-catalyzed reactions, organic halides are most widely used. In Grignard reactions, Mg(0) metal reacts with organic halides of sp carbons (alkyl halides) more easily than halides of sp carbons (aryl and alkenyl halides). On the other hand, Pd(0) complexes react more easily with halides attached to sp carbons, namely aryl and alkenyl halides. In addition, several pseudohalides are used as well. They undergo facile oxidative addition to Pd(0) to form Pd complexes which have cr-Pd-carbon bonds. Scheme 3.1 summarizes the oxidative addition of phenyl halides and pseudohalides to form phenylpalladium halides. Aryl iodides and bromides have been used widely. 

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