ORGN 174

Toward a protecting group-free halogen-metal exchange reaction: Synthetic and structual study of dianion-type zincate, tBu₄ZnLi₂

Taniyuki Furuyama, Yotaro Matsumoto, Tomohiko Ohwada, and Masanobu Uchiyama. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan

A versatile preparation method for aromatic zincate compounds through 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 reaction followed by electrophilic trapping (with allyl bromide or benzaldehyde) and transition metal catalyzed reaction proved a powerful tool for C-C bond formation on functionalized aromatic rings. Further details in preparation, application, and structural analysis of this new zincate will be shown in the presentation.

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006