Toward a Protecting-Group-Free Halogen−Metal Exchange Reaction: Practical, Chemoselective Metalation of Functionalized Aromatic Halides Using Dianion-type Zincate, tBu4ZnLi2
- 8 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (26), 8404-8405
- https://doi.org/10.1021/ja058246x
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.This publication has 9 references indexed in Scilit:
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