Toward a Protecting-Group-Free Halogen−Metal Exchange Reaction: Practical, Chemoselective Metalation of Functionalized Aromatic Halides Using Dianion-type Zincate, tBu4ZnLi2
Journal of the American Chemical Society2006Vol. 128(26), pp. 8404–8405
Citations Over TimeTop 10% of 2006 papers
Abstract
A versatile preparation method for aromatic zincate compounds through a halogen-zinc exchange reaction using dilithium tetra-tert-butylzincate (tBu4ZnLi2) has been developed. This reagent permits efficient preparation of highly functionalized aromatic zincates, particularly, those with electrophilic functional groups, such as ester, amide, alcohol, and phenol. Halogen-zinc exchange reactions followed by electrophilic trapping (with allyl bromide or benzaldehyde) proved to be a powerful tool for C-C bond formation on functionalized aromatic rings. The functionalized aromatic zincate intermediate was also found to undergo copper- and palladium-catalyzed C-C bond-forming reactions with good yields and high chemoselectivity.
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