Mild Friedel–Crafts Reactions inside a Hexameric Resorcinarene Capsule: C?Cl Bond Activation through Hydrogen Bonding to Bridging Water Molecules
A novel catalytic feature of a hexameric resorcinarene capsule is highlighted. The self-assembled cage was exploited to promote the Friedel–Crafts benzylation of several arenes and heteroarenes with benzyl chloride under mild conditions. Calculations showed that there are catalytically relevant hydrogen-bonding interactions between the bridging water molecules of the capsule and benzyl chloride, which is fundamental for the activation of the C?Cl bond. The capsule controls the reaction outcome. Inside the inner cavity of the capsule, N-methylpyrrole is preferentially benzylated in the unusual β-position while mesitylene reacts faster than 1,3-dimethoxybenzene despite the greater π-nucleophilicity of the latter compound.
Platinum-catalyzed formation of cyclic-ketone-fused indoles from N-(2-alkynylphenyl)lactams
(Chemical Equation Presented) An oxygen atmosphere aids the efficient formation of highly substituted ring-fused indoles by the versatile title reaction through an initial cyclization followed by the sequential migration of two groups. The cycloisomerizat
Li, Guotao,Huang, Xiaogen,Zhang, Liming
p. 346 - 349
(2008/09/18)
Indol-2-yltributylstannane: A versatile reagent for 2-substituted indoles
A general method for 2-substituted indoles via the palladium-catalyzed coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tributylstannane (1) reacts with a variety of electrophiles under very mild conditions. [N-tert-Butoxycarbonyl)indol-2
Labadie,Teng
p. 4250 - 4254
(2007/10/02)
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