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Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide–Catalyzed Hydrosilylation of Terminal Epoxides

preprint
submitted on 03.10.2019 and posted on 07.10.2019 by Keri Steiniger, Tristan Lambert
The 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.

Funding

Catalytic Platforms Using Aromatic Ions and Other Charged Species

National Institute of General Medical Sciences

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History

Email Address of Submitting Author

thl36@cornell.edu

Institution

Cornell University

Country

United States of America

ORCID For Submitting Author

0000-0002-7720-3290

Declaration of Conflict of Interest

no conflict of interest

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