Showing papers by "Fumitoshi Kakiuchi published in 2013"
TL;DR: The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products.
Abstract: The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C–H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.
68 citations
TL;DR: The first catalytic intermolecular [2 + 2] cycloaddition of terminal alkynes with electron-deficient alkenes is reported, giving cyclobutenes from various substrates having polar functional groups in high yields with complete regioselectivity.
54 citations
TL;DR: In this paper, the reactivity of various o-acylaniline derivatives with ruthenium complexes was examined, and it was found that electron-donating substituents increase the relative facileness of the C-N bond cleavage in both stoichiometric and catalytic reactions.
37 citations
TL;DR: In this paper, two new catalytic transformations of anilines via oxidative addition of C-N bonds to ruthenium centers were developed via reductive deaminatoindeamination of N-alkylated o-acylanilines.
25 citations
24 citations
TL;DR: In this article, an 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes.
Abstract: An 8-quinolinolato rhodium catalyst was found to be effective for head-to-tail selective dimerization of arylacetylenes. Formation of substituted cyclopentene and allene derivatives via alkyne dimerization and subsequent addition of malonates was also catalyzed by the 8-quinolinolato rhodium catalyst in the presence of cesium fluoride. One-pot reaction using palladium-catalyzed alkyne dimerization in conjunction with rhodium-catalyzed addition of malonates was also possible.
17 citations
TL;DR: In this paper, the catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described, using a palladium-1,10-phenanthroline catalyst to form five-membered ring products.
Abstract: The catalytic construction of carbon–carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium–1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon–hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.
5 citations
TL;DR: The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio-and stereoselectively through a directed C-H bond cleavage to produce the corresponding ortho-alkenylated products as discussed by the authors.
Abstract: The ruthenium-catalyzed coupling reactions of benzamides with alkynes in the presence of acetic acid as a promoter smoothly proceeded regio- and stereoselectively through a directed C–H bond cleavage to produce the corresponding ortho-alkenylated products. Phenylpyrazoles and related substrates also underwent a similar coupling to give dialkenylated products selectively. Several competitive experiments were performed to obtain mechanistic insight into both the mono- and dialkenylation reactions.
4 citations
2 citations
TL;DR: In this article, an 8-quinolinolato rhodium catalyst was used for head-to-tail selective dimerization of arylacetylenes (I).
Abstract: An 8-quinolinolato rhodium catalyst is found to be effective for head-to-tail selective dimerization of arylacetylenes (I).
1 citations
TL;DR: The title reaction of cyclobutenes is completely regioselective and various combinations of terminal alkynes and acrylates can be used to obtain high yields as discussed by the authors.
Abstract: The title reaction, affording cyclobutenes in high yields, is completely regioselective, and various combinations of terminal alkynes and acrylates can be used.