Open AccessPrimary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides
Author(s) -
Keri A. Steiniger,
Tristan H. Lambert
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c03029
Subject(s) - chemistry , hydrosilylation , catalysis , regioselectivity , nickel , ligand (biochemistry) , primary (astronomy) , lewis acids and bases , terminal (telecommunication) , combinatorial chemistry , organic chemistry , derivative (finance) , financial economics , telecommunications , biochemistry , physics , receptor , astronomy , computer science , economics
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.