Electrophilic Amination of Organozinc Halides

The only examples of electrophilic amination of organozinc compounds described in the literature correspond to the reaction of an excess of diethyl/ diisopropyl zinc with several chloroamines [61]. The reaction afforded moderate to low yields of substitution products, often as a mixture of amines [62,63]. On the other hand, electrophilic amination using dialkyl azodicarboxylates has been reported for other nucleophilic species, including lithium enolates and silyl enol ethers [64-70]. 

2g as a white solid (Table 3.17,2g, 80%). In the case of aromatic bromides, reflux conditions were required (Table 3.17, h and i). An excess of active zinc was used in all cases to assure that oxidative addition went to completion within reasonable times. Di-tert-butyl hydrazinodicarboxylates 

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