Journal ArticleDOI
The Ruthenium-Catalyzed Addition of C-H Bonds in Aromatic Nitriles to Olefins
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In this article, the reaction of aromatic nitriles with triethoxyvinylsilane is described in the presence of a Ru(H)2(CO)(PPh3)3-catalyst to give the corresponding C-H/olefin coupling products.Abstract:
The reaction of aromatic nitriles with triethoxyvinylsilane proceeded in the presence of a Ru(H)2(CO)(PPh3)3-catalyst to give the corresponding C-H/olefin coupling products in high yields. The nitrile group is capable of directing the ruthenium to the ortho C-H bond via π-bonded mode.read more
Citations
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Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
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Ru-, Rh-, and Pd-Catalyzed C-C Bond Formation Involving C-H Activation and Addition on Unsaturated Substrates: Reactions and Mechanistic Aspects
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Transition-Metal-Catalyzed C–H Alkylation Using Alkenes
TL;DR: This Review summarizes transition-metal-catalyzed alkylations of various carbon-hydrogen bonds (addition of C-H bonds across olefins) using regular ole fins or 1,3-dienes up to May 2016.
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Non-Metathesis Ruthenium-Catalyzed C−C Bond Formation
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Ru3(CO)12-Catalyzed Coupling Reaction of sp3 C−H Bonds Adjacent to a Nitrogen Atom in Alkylamines with Alkenes
Naoto Chatani,Taku Asaumi,Shuhei Yorimitsu,Tsutomu Ikeda,and Fumitoshi Kakiuchi,Shinji Murai +5 more
TL;DR: Catalytic reactions which involve the cleavage of an sp(3) C-H bond adjacent to a nitrogen atom in N-2-pyridynyl alkylamines are described and the substitution of an electron-withdrawing group on the pyridine ring as well as a substitution adjacent to the sp(2) nitrogen in the pyrsidine ring dramatically retards the reaction.
References
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Journal ArticleDOI
Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins
Shinji Murai,Fumitoshi Kakiuchi,S. Sekine,Yasuo Tanaka,Asayuki Kamatani,Motohiro Sonoda,Naoto Chatani +6 more
TL;DR: The selective cleavage of carbon-hydrogen bonds in organic compounds is a critical step in many organic syntheses, and is particularly important in the conversion of hydrocarbons to useful organic compounds.
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Reactions of transition metal-coordinated nitriles
TL;DR: The reaction chemistry of nitriles with transition metal complexes is reviewed in this paper, where the authors survey data published during the period 1977-early 1994 on new reaction processes such as insertion into metal-hydrogen and carbon bonds, coupling between one nitrile and an unsaturated metal fragment, reduction to amines, attack by protic and aprotic nucleophiles and electrophilic attack as well as some catalytic transformations.
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Organonitrile complexes of transition metals
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Catalytic Addition of Aromatic Carbon–Hydrogen Bonds to Olefins with the Aid of Ruthenium Complexes
Fumitoshi Kakiuchi,S. Sekine,Yasuo Tanaka,Asayuki Kamatani,Motohiro Sonoda,Naoto Chatani,Shinji Murai +6 more
TL;DR: In this paper, the importance of the coordination of the oxygen atom of the ketone to ruthenium and the intervention of a cyclometallation intermediate are suggested. But the results of the deuterium labeling experiment using acetophenone-d5 and triethoxyvinylsilane are limited.
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Catalytic C-H/olefin coupling
Shinji Murai,Fumitoshi Kakiuchi,S. Sekine,Yasuo Tanaka,Asayuki Kamatani,Motohiro Sonoda,Naoto Chatani +6 more
TL;DR: The cleavage and addition of ortho C-H bonds in various aromatic compounds such as ketones, esters, imines, imidates, nitrile, and aldehydes to olefins and acetlylenes can be achieved catalytically with the aid of ruthenium catalysts.