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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 -78C 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.