Showing papers by "Fumitoshi Kakiuchi published in 2016"
TL;DR: The cross-coupling of maleimides with electron-deficient alkenes such as acrylates proceeds smoothly under ruthenium catalysis and provides a simple, straightforward synthetic method for preparing alkylidene succinimide derivatives.
24 citations
TL;DR: Palladium catalysts possessing pyridine-oxazoline ligands were found to catalyze the chain-walking cycloisomerization of 1,n-dienes to form five-membered rings and were particularly effective for t...
Abstract: Palladium catalysts possessing pyridine–oxazoline ligands were found to catalyze the chain-walking cycloisomerization of 1,n-dienes to form five-membered rings and were particularly effective for t...
17 citations
TL;DR: In this article, the synthesis of rhodium(I) complexes bearing a phosphine-quinolinolate ligand and the isolation of two classes of important intermediates in the anti-Markovnikov hydroamination of terminal alkynes with secondary amines: vinylidene-bridged dirhodium complexes and (amino)carbene complexes.
14 citations
TL;DR: Electrochemical measurements indicated that these compounds showed low-lying lowest unoccupied molecular orbital energy levels, which could be fine-tuned by the combination of central unit.
13 citations
TL;DR: In this article, the palladium-catalyzed cycloisomerization of 1,n-dienes was shown to achieve carbon-carbon bond formation at unreactive sp3-carbons in small organic molecules via chain walking.
Abstract: Carbon–carbon bond formation at unreactive sp3-carbons in small organic molecules via chain walking was achieved for the palladium-catalyzed cycloisomerization of 1,n-dienes. Various 1,n-dienes (n = 7–14) such as those containing cyclic alkenes, acyclic internal alkenes, and a trisubstituted alkene can be used for the chain-walking cycloisomerization/hydrogenation process, and five-membered ring compounds including simple cyclopentane and pyrrolidine derivatives can easily be prepared. Chain walking over a tertiary carbon was also found to be possible in the cycloisomerization. It is not necessary for the linker portion of the diene to contain a quaternary center, and diene substrates with two alkene moieties linked by a tertiary carbon or a nitrogen atom can also be used as substrates. Column chromatography using silica gel containing silver nitrate was found to be effective for isolating some of the cycloisomerization products without hydrogenation. Deuterium-labeling experiments provided direct evidenc...
8 citations
TL;DR: In this paper, a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C-H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups.
Abstract: We report here a method for direct catalytic introduction of simple α-acylalkyl groups via rhodium-catalyzed C–H functionalization with cyclic alkenyl carbonates, synthetic equivalents to enolates bearing leaving groups. The reaction proceeded smoothly without using bases to give α-aryl ketones in high yields. Various nitrogen-containing aromatic rings and amide groups serve as directing groups. 3-Substituted isocoumarins can also be prepared by one-pot C–H functionalization/cyclization.
4 citations
TL;DR: Palladium catalysts possessing pyridine-oxazoline ligands were found to catalyze the chain-walking cycloisomerization of 1,n-dienes to form five-membered rings and were particularly effective for t...
Abstract: Palladium catalysts possessing pyridine–oxazoline ligands were found to catalyze the chain-walking cycloisomerization of 1,n-dienes to form five-membered rings and were particularly effective for t...