Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

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 range of substrates including both terminal and nonterminal 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.

Automated summary

A new method for efficient and regioselective hydrosilylation of epoxides using a PCCP nickel complex and Lewis acid co-catalyst has been reported, leading to the formation of unbranched, primary alcohols from terminal, monosubstituted epoxides. The method is shown to work with a variety of substrates, both terminal and nonterminal epoxides, and a mechanistic rationale is provided for this novel use of a PCCP derivative as a ligand for transition-metal catalysis.