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31.34.1.1.5 Method 5: Electrophilic Hydrazination of Metalated Arenes

DOI: 10.1055/sos-SD-031-01959

Begtrup, M.; Rasmussen, L. K.Science of Synthesis, (2007311781.

Electrophilic hydrazination of metalated arenes by dialkyl azodicarboxylates proceeds smoothly to give arylhydrazines 9 using aryllithium reagents,[‌120‌] arylmagnesium bromides (Scheme 10),[‌114‌] arylboronic acids,[‌121‌] or arylzinc chlorides.[‌122‌] A protocol generating the aryllithium by brominelithium exchange, using excess lithium base, tolerates the presence of a carboxylic acid group.[‌123‌]

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