An
iron-catalyzed borrowing hydrogen strategy has been applied
in the synthesis of β-branched carbonyl compounds. Various secondary
benzylic and aliphatic alcohols have been used as alkylating reagents
under mild reaction conditions. The ketones have been isolated in
good to excellent yield. Deuterium labeling experiments provide evidence
that the alcohol is the hydride source in this reaction and that no
reversible step or hydrogen/deuterium scrambling takes place during
the process.
β-Branched
alkylated alcohols have been prepared in good
yields using a double-hydrogen autotransfer strategy in the presence
of our diaminocyclopentadienone iron tricarbonyl complex Fe1. The alkylation of some 2-arylethanol derivatives was successfully
addressed with benzylic alcohols and methanol as alkylating reagents
under mild conditions. Deuterium labeling experiments suggested that
both alcohols (2-arylethanol and either methanol or benzyl alcohol)
served as hydrogen donors in this cascade process.
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