Dimethylzirconocene methylates alkyldichloro- and dialkylchloroboranes selectively to give the corresponding alkyldimethyl- and dialkylmethylboranes in essentially quantitative yields.  This is especially important in the methylation of primary alkyldichloroboranes which undergo significant redistribution with methyllithium and methyl Grignard reagents.  The reaction is very fast in non-coordinating hydrocarbon solvents, precipitating the dichlorozirconocene.  The low reactivity of dimethylzirconocene to other functional groups compliments the more reactive organometallic reagents.  The methylation of vinylboranes is more sensitive towards redistribution than alkylmethylboranes; however, dimethylzirconocene gives very good selectivity to the vinyldimethylborane with minimal amount of redistribution products

Mild and selective addition of methyl groups to alkylhaloboranes using dimethylzirconocene

241st National Meeting (2011)

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