Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of enones
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Recent Literature
Aromatic α,β-unsaturated ketones are synthesized efficiently by
palladium-catalyzed cross-coupling reaction of arylboronic acids with
α,β-unsaturated acyl chlorides in the presence of K3PO4
hydrate in toluene.
Y. Urawa, K. Nishiura, S. Souda, K. Ogura, Synthesis, 2003,
2882-2885.
A N-heterocyclic carbene catalyzed the synthesis of aldol products in good
yields involving carbonyl umpolung of enals to form nucleophiles, which attack
electrophilic terminal epoxides, regioselectively. These aldols have been used
in a facile and highly cis-selective synthesis of tetrahydropyran-4-ones.
L. D. S. Yadav, S. Singh, V. K. Rai, Synlett, 2010,
240-246.
A new method for the synthesis of organoborates starting from α,β-unsaturated
acetals was developed. The available alkoxy-functionalized butadienyl- and
styrylboronic esters cross couple effectively with a broad spectrum of aryl
halides under mild conditions. This method provides an effective
approach to aromatic ketones.
P. B. Tivola, A. Deagostino, C. Prandi, P. Venturello, Org. Lett.,
2002, 4, 1275-1277.
A chemoselective addition of halomethyllithium carbenoids to Weinreb amides at
-78°C enables a straightforward synthesis of variously functionalized
α,β-unsaturated α'-haloketones. The exceptional stability of the intermediate
furnished by the N-methoxy group does not allow a 2nd addition of LiCH2X
and thus prevents from formation of carbinols.
V. Pace, L. Castoldi, W. Holzer, J. Org. Chem., 2013,
78, 7764-7770.
A regioselective intermolecular hydroacylation of vinalarenes, in which
symmetric and mixed carboxylic anhydrides are used as acyl donors, is
promoted by a cationic rhodium catalyst ligated by triphenylarsine.
Y.-T. Hong, A. Barchuk, M. J. Krische, Angew. Chem. Int. Ed., 2006,
45, 6885-6888.
A regioselective intermolecular hydroacylation of vinalarenes, in which
symmetric and mixed carboxylic anhydrides are used as acyl donors, is
promoted by a cationic rhodium catalyst ligated by triphenylarsine.
Y.-T. Hong, A. Barchuk, M. J. Krische, Angew. Chem. Int. Ed., 2006,
45, 6885-6888.
