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Metal‐Free Hydrosilylation of Ketenes with Silicon Electrophiles: Access to Fully Substituted Aldehyde‐Derived Silyl Enol Ethers
Author(s) -
Roy Avijit,
Oestreich Martin
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100877
Subject(s) - hydrosilylation , enol , silylation , chemistry , aldehyde , electrophile , borane , lewis acids and bases , silyl enol ether , organic chemistry , polymer chemistry , medicinal chemistry , catalysis
Little‐explored hydrosilylation of ketenes promoted by main‐group catalysts is reported. The boron Lewis acid tris(pentafluorophenyl)borane accelerates the slow uncatalyzed reaction of ketenes and hydrosilanes, thereby providing a convenient access to the new class of β,β‐di‐ and β‐monoaryl‐substituted aldehyde‐derived silyl enol ethers. Yields are moderate to high, and Z configuration is preferred. The corresponding silyl bis‐enol ethers are also available when using dihydrosilanes. The related trityl‐cation‐initiated hydrosilylation involving self‐regeneration of silylium ions is far less effective.