On the Regioselectivity of the Nickel-Catalyzed Insertion of Alkynes into the Carbon-Carbon Bond of Oxetan-3-one
The study of the regioselectivity of insertion of unsymmetrical alkynes into the carbon-carbon bond of oxetan-3-one in the presence of a nickel catalyst has revealed a strong directing effect of a 2-thienyl substituent. This effect is larger than those of 2-vinylbenzene, trimethylsilyl, aryl, or 3-thienyl groups.
Barday, Manuel,Janot, Christopher,Clare, Daniel,Carr-Knox, Caitlin,Higginson, Bradley,Ho, Kelvin Y. T.,A?ssa, Christophe
p. 3582 - 3589
(2017/08/16)
Regioselective cycloaddition of 3-azetidinones and 3-oxetanones with alkynes through nickel-catalysed carbon-carbon bond activation
Get in the ring! The first examples of transition-metal-catalysed C-C bond activation of 3-azetidinones and 3-oxetanones are reported. In the presence of a nickel catalyst and alkynes, a regioselective and high-yielding [4+2] cycloaddition occurs, leading to the formation of pyridinones, pyranones and eventually 4,5-disubstituted 3-hydroxypyridines (see scheme). Copyright
Ho, Kelvin Y. T.,Aissa, Christophe
supporting information; experimental part
p. 3486 - 3489
(2012/05/19)
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