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Iridium‐Catalyzed Coupling Reaction of Primary Alcohols with 2‐Alkynes Leading to Hydroacylation Products
Author(s) -
Hatanaka Shintaro,
Obora Yasushi,
Ishii Yasutaka
Publication year - 2010
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.200902646
Subject(s) - hydroacylation , iridium , isomerization , regioselectivity , catalysis , dehydrogenation , chemistry , coupling reaction , intermolecular force , organic chemistry , primary (astronomy) , photochemistry , medicinal chemistry , aldehyde , physics , molecule , astronomy
A novel iridium‐catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2‐alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β‐unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ‐unsatutated ketones and then isomerisation, which leads to the hydroacylation products.