The iodine-metal exchange reaction on cubane was examined using various lithium organozincates. Among these, the dianionic zincate, n-BuZnLi, gave optimum results. The resulting cubyl metal species could be converted into various cubane derivatives via addition reactions with electrophiles, such as an organohalide or aldehyde. The potential functional group tolerance of organozincates lends this protocol to the synthesis of polyfunctionalized cubane derivatives.
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| http://dx.doi.org/10.1021/acs.orglett.8b03721 | DOI Listing |
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