Boron/zinc exchange for the conjugate arylation of unsaturated Meldrum's acid derivatives
An approach for the conjugate arylation reaction of unsaturated Meldrum's acid derivatives is reported. The reaction takes place through a Boron-Zinc exchange reaction between arylboronic acids and diethylzinc and the subsequent transfer of thus generated reactive aryl groups to the β-position of the double bond of the Meldrum's derivatives. The compounds obtained are valuable synthetic intermediates and can give rise to bioactive molecules such as β,β-disubstituted carboxylic acids and amides.
Jardim, Micaela,Baldassari, Lucas L.,Contreira, Maria Eduarda,Moro, Angélica V.,Lüdtke, Diogo S.
(2020/01/31)
Carbon-based leaving group in substitution reactions: Functionalization of sp3-hybridized quaternary and tertiary benzylic carbon centers
Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic Csp 3-Csp3 bonds into Csp3-X bonds (X = C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically >90%).
Mahoney, Stuart J.,Lou, Tiantong,Bondarenko, Ganna,Fillion, Eric
p. 3474 - 3477
(2012/09/05)
Hydrogenolysis of unstrained carbon-carbon σ bonds: Stereoselective entry into benzylic tertiary centers
(Chemical Equation Presented) The modification of sp3-hybridized carbon centers through Pd-catalyzed reductive cleavage of unstrained carbon-carbon @ bonds is described. From the hydrogenolysis of benzyl Meldrum's acids bearing an all-carbon be
Wilsily, Ashraf,Nguyen, Yen,Fillion, Eric
supporting information; experimental part
p. 15606 - 15607
(2010/01/30)
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