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Iron‐Catalysed Chemo‐, Regio‐, and Stereoselective Hydrosilylation of Alkenes and Alkynes using a Bench‐Stable Iron(II) Pre‐Catalyst
Author(s) -
Greenhalgh Mark D.,
Frank Dominik J.,
Thomas Stephen P.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300827
Subject(s) - hydrosilylation , chemistry , catalysis , markovnikov's rule , stereoselectivity , silane , olefin fiber , reagent , yield (engineering) , organic chemistry , regioselectivity , materials science , metallurgy
The chemo‐, regio‐, and stereoselective iron‐catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41–96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ , thus providing a simple and practical methodology for iron‐catalysed hydrosilylation. The silane products can be oxidised to the anti‐Markovnikov product of olefin hydration, and the one‐pot iron‐catalysed hydrosilylation–oxidation of olefins to give silane(di)ols directly is also reported. The iron pre‐catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 mol h −1 . Initial mechanistic studies indicate an iron(I) active catalyst.