Showing papers by "Fumitoshi Kakiuchi published in 2017"
TL;DR: The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions and the use of 5,7-dichloro-8-quinlinyl group as directing group was effective for the selective chlorination.
Abstract: The palladium-catalyzed ortho-selective chlorination of N-quinolinylbenzamide derivatives with hydrochloric acid was achieved under anodic oxidation conditions. The use of 5,7-dichloro-8-quinolinyl group as directing group was effective for the selective chlorination, and the reaction was applicable to benzamide derivatives bearing various functional groups. Synthesis of vismodegib was also completed using the palladium-catalyzed electrochemical C–H chlorination in two different steps.
69 citations
TL;DR: A C-H alkylation reaction, in which the coupling of aromatic ketones with alkenes proceeds in the presence of only a simple Fe(PMe3)4 catalyst, with excellent regioselectivity under relatively mild reaction conditions.
Abstract: We report here on a C–H alkylation reaction, in which the coupling of aromatic ketones with alkenes proceeds in the presence of only a simple Fe(PMe3)4 catalyst. The anti-Markovnikov addition of ortho C–H bonds in various ketones occurs with excellent regioselectivity under relatively mild reaction conditions. A strikingly wide variety of alkenes can be used for this reaction, and the high-yielding anti-Markovnikov addition of aromatic C–H bonds to enol ethers was achieved for the first time using this catalyst system.
63 citations
TL;DR: A series of ruthenium complexes, RuHCl(CO)(PAr3)3 and RuH2(CO), containing various triarylphosphines were synthesized for direct arylation of sterically congested ortho C-H bonds as discussed by the authors.
29 citations
TL;DR: The ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds was applicable to a variety of arylboronates and aromatic Ketones and proceeds with high regio- and chemoselectivities.
28 citations
TL;DR: Ruthenium-catalyzed C-H arylation of aromatic nitriles with arylboronates is described, and the cyano group was also found to function as a directing group for cleavage of C-O bonds in aRYl ethers.
Abstract: Ruthenium-catalyzed C–H arylation of aromatic nitriles with arylboronates is described. The use of RuH2(CO){P(4-MeC6H4)3}3 as a catalyst provided higher yields of the ortho arylation products than the conventional RuH2(CO)(PPh3)3 catalyst. The arylation takes place mostly at the ortho positions, but unprecedented para arylation was also partially observed to give ortho,para diarylation products. In addition to C–H bond cleavage, the cyano group was also found to function as a directing group for cleavage of C–O bonds in aryl ethers.
20 citations
TL;DR: In this article, a review of transition-metal-catalyzed efficient and selective C−H functionalization by electrochemical reactions is presented, where the authors briefly survey the literature.
Abstract: Efficient, selective, transition-metal-catalyzed C−H functionalizations have been widely studied and are recognized as atom- and step-economical tools in organic synthesis. During the past two decades, a variety of catalytic reactions involving C−H bond cleavage have been developed. In this review, we briefly survey studies dealing with transition-metal-catalyzed efficient and selective C−H functionalization by electrochemical reactions.
18 citations
TL;DR: A novel (PNO): phosphine-quinolinolate/CuBr tandem catalyst system was developed for facile synthesis of α-monosubstituted propargylamines from aliphatic terminal alkynes and secondary amines.
Abstract: A novel (PNO)Rh/CuBr (PNO: phosphine-quinolinolate) tandem catalyst system was developed for facile synthesis of α-monosubstituted propargylamines from aliphatic terminal alkynes and secondary amines. Various terminal alkynes and amines were applicable to this reaction and the corresponding propargylamines were obtained in good yields.
11 citations
TL;DR: An efficient two-step procedure consisting of a Corey-Chaykofsky reaction and subsequent dehydrative aromatization afforded derivatives of dibenzo[h,rst]pentaphenes and dibanzo[fg,qr]pentacenes, and Hole-transporting characteristics were observed for a device with a bottom-contact configuration that was fabricated from one of these polycyclic aromatic hydrocarbons.
9 citations
TL;DR: In this paper, tetraarylanthracenes containing several fluoro groups were synthesized using the ruthenium-catalyzed C-O or C-F arylation with arylboronates.
Abstract: Tetraarylanthracenes containing several fluoro groups were synthesized using the ruthenium-catalyzed C–O or C–F arylation with arylboronates and their structural and spectroscopic studies were conducted. The RuH2(CO)(PPh3)3-catalyzed C–O arylation of aromatic ketones was found to be effective for the introduction of aryl groups containing multiple fluoro groups. Anthracenes possessing fluorinated aryl groups were prepared in two steps from 1,4,5,8-tetramethoxyanthraquinone by C–O arylation and reduction of the carbonyl groups. A tetraphenylanthracene containing a fluorinated anthracene moiety was also prepared using C–F phenylation of octafluoroanthraquinone. Single-crystal X-ray diffraction analysis showed that the positions of fluoro groups on the tetraarylanthracenes lead to notable difference in the crystal packing structures. The larger difference between the tetraarylanthracenes was observed in the fluorescence spectra in the solid state than those in chloroform.
7 citations