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Direct Acetophenone–Acetophenone Crossed Aldol Reaction and Aldol Self‐Reaction Promoted by a Tethered Ru–S Complex
Author(s) -
Pommerening Phillip,
Stahl Timo,
Oestreich Martin
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800132
Subject(s) - aldol reaction , chemistry , acetophenone , silyl enol ether , enol , aldol condensation , ketone , adduct , silylation , cyclohexanone , reagent , organic chemistry , medicinal chemistry , catalysis
The serendipitous discovery of aldol reactions of two methyl ketones is reported. The tertiary aldols do form during the dehydrogenative Si–O coupling of the corresponding enolizable ketone and a hydrosilane. The ratio of the expected silyl enol ether and the aldol adduct depends on various reaction parameters but is particularly pronounced with the hydrosilane as the limiting reagent. Aside from aldol self‐reactions, the direct crossed aldol reaction is, in principle, also possible. The hydrosilane can be replaced by a hydroborane, then involving a boron enolate as the enol component.