Ruthenium-Catalyzed β-Allyl Elimination Leading to Selective Cleavage of a Carbon−Carbon Bond in Homoallyl Alcohols

Kondo, Teruyuki; Kodoi, K.; Nishinaga, Eiji; Okada, Takumi; Morisaki, Yasuhiro; Watanabe, Yoshihisa; Mitsudo, Take‐aki

doi:10.1021/ja980714y

Cited by 156 publications

(92 citation statements)

References 13 publications

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“…In the course of our study of © 3 -allylruthenium chemistry, 4e,23 a catalytic deallylation of tertiary homoallyl alcohols 1 to ketones 2 and alkenes was found, in which the key step of the present reaction is ¢-carbon elimination (Scheme 2). 24 The present reaction is the first example of the transition-metal-complex-catalyzed cleavage of a carboncarbon bond without ring strain. This reaction was applicable to opening cyclic homoallyl alcohols to linear ketones, giving a new strategy for the ring-opening reaction.…”

Section: Ruthenium-and Rhodium-catalyzed Cleavage Of Carboncarbon Bonmentioning

confidence: 78%

“…More recently, we developed a heterogeneous Ru/CeO 2 catalyst which has high catalytic activity for allyl-transfer from tertiary homoally alcohols to aldehydes. 25 This heterogeneous catalyst can be easily recovered and reused, and in sharp contrast to the homogeneous ruthenium catalyst, 24 neither carbon monoxide pressure nor allylic acetates are needed.…”

Section: Ruthenium-and Rhodium-catalyzed Cleavage Of Carboncarbon Bonmentioning

confidence: 99%

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New Catalytic Performances of Ruthenium and Rhodium Complexes Directed toward Organic Synthesis with High Atom Efficiency

Kondo¹

2011

Bulletin of the Chemical Society of Japan

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Low-valent ruthenium complexes often show intriguing and characteristic catalytic activity for novel organic transformations with high atom efficiency. The design and synthesis of novel low-valent ruthenium complexes having a variety of electron-donating and/or electron-withdrawing ligands is most promising strategy. Several ruthenium catalysts achieved the construction of novel functional organic molecules through cleavage of carboncarbon single bonds, cocyclization of alkynes, alkenes, and/or carbon monoxide, and co-oligomerization of different alkenes without formation of by-products, which meets green and sustainable requirements for organic synthesis in the 21st century. Note that many findings in ruthenium catalysis have opened the door to a new field of rhodium-catalyzed synthetic organic chemistry, represented by cocyclization of alkynes and heterocumulenes.

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Section: Ruthenium-and Rhodium-catalyzed Cleavage Of Carboncarbon Bonmentioning

confidence: 78%

Section: Ruthenium-and Rhodium-catalyzed Cleavage Of Carboncarbon Bonmentioning

confidence: 99%

New Catalytic Performances of Ruthenium and Rhodium Complexes Directed toward Organic Synthesis with High Atom Efficiency

Kondo¹

2011

Bulletin of the Chemical Society of Japan

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“…[21] This microreview does not include cleavage reactions of unstrained C-C bonds. [22,23] 2. Strain-Driven Cleavage of the C-C Bond of 2,5-Norbornadienes 2.1.…”

Section: Rhmentioning

confidence: 99%

Ruthenium‐ and Rhodium‐Catalyzed Strain‐Driven Cleavage and Reconstruction of the C–C Bond

Kondo

2016

Eur J Org Chem

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“…Therefore, the application of supported catalysts for highly selective organic reactions such as C _ C bond formation via the activation of stable C _ H or C _ C bonds still remains a challenge. In this context, we have recently found that a simple oxide-supported catalyst, Ru/ CeO2, is quite effective for transfer allylation from homoallylic alcohols to aldehydes 34) , for which homogeneous ruthenium 35) , rhodium 36) 38) , and copper 39) complex catalysts have been reported to be effective. The success of our first attempt prompted us to examine the effectiveness of Ru/CeO2 as a solid catalyst alternative to low-valent ruthenium complex catalysts, and we have revealed that Ru/CeO2 could realize various organic transformations, including reactions that proceed C _ H bond activation 40) 46) .…”

Section: Introductionmentioning

confidence: 99%

グリーン有機分子変換プロセスを指向したセリア担持ルテニウム触媒の開発

Wada

Miura

Hosokawa

et al. 2013

J. Jpn. Petrol. Inst.

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Solid Ru/CeO2 catalysts, which are effective for the catalysis of various highly atom-efficient organic transformations such as dehydrogenative synthesis of indole, regio-and stereo-selective coupling of unsaturated hydrocarbons, C _ C bond-forming reactions via the activation of aromatic C _ H bonds, and selective addition of carboxylic acids to alkynes, have been developed. For these reactions, CeO2-supported and, in some cases, ZrO2-supported catalysts show excellent activities, whereas ruthenium catalysts on other oxide supports are not effective. Spectroscopic studies have revealed that various types of catalytically active, low-valent ruthenium species are generated from ruthenium(IV) oxo species that are exclusively formed on the surface of CeO2 under appropriate conditions. These solid ruthenium catalysts can be recycled without loss of activity or significant leaching of ruthenium species into the solution, and these features, as well as the wide range of applicable reactions, make the present catalytic system quite attractive from both practical and environmental perspectives.

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Ruthenium-Catalyzed β-Allyl Elimination Leading to Selective Cleavage of a Carbon−Carbon Bond in Homoallyl Alcohols

Cited by 156 publications

References 13 publications

New Catalytic Performances of Ruthenium and Rhodium Complexes Directed toward Organic Synthesis with High Atom Efficiency

New Catalytic Performances of Ruthenium and Rhodium Complexes Directed toward Organic Synthesis with High Atom Efficiency

Ruthenium‐ and Rhodium‐Catalyzed Strain‐Driven Cleavage and Reconstruction of the C–C Bond

グリーン有機分子変換プロセスを指向したセリア担持ルテニウム触媒の開発

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