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Ni_PCCP.docx (585.17 kB)
Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide–Catalyzed Hydrosilylation of Terminal Epoxides
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 03.10.2019 and posted on 07.10.2019by Keri Steiniger, Tristan Lambert
efficient and regioselective hydrosilylation of epoxides co-catalyzed by a
pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is
reported. This method allows for the
reductive opening of terminal, monosubstituted epoxides to form unbranched,
primary alcohols. A screen of diamide
PCCP ligands revealed a correlation of steric demand and regioselectivity, with
smaller ligands being optimal, while the addition of Lewis acid enabled
efficient reactions at room temperature.
A range of substrates including both terminal and non-terminal epoxides
are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP
derivative as a ligand for transition metal catalysis.