Non-cryogenic metalation of aryl bromides bearing proton donating groups: Formation of a stable magnesio-intermediate
Bromine-metal exchange of o-bromobenzoic acid (1) with Bu2Mg followed by n-BuLi was successfully carried out at non-cryogenic temperature (>-20°C), and gave a stabilized metal species which smoothly reacted with several electrophiles. This methodology expanded to several other bromides bearing proton donating groups (PDGs).
METHOD OF SUBSTITUENT INTRODUCTION THROUGH HALOGEN-METAL EXCHANGE REACTION
A method of exchanging a halogen atom of a halide, which has a group containing an acidic proton and in which one or more halogen atom(s) is/are substituted on a carbon atom of the carbon-carbon double bond, with a metal atom by halogen-metal-exchange reaction and introducing an electrophilic reagent into the carbon atom to which the metal atom is attached. The above method is an industrially excellent method of introducing a substituent by halogen-metal exchange reaction.
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(2010/02/10)
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