Catalytic Carbon−Carbon Bond Activation of<i>sec</i>-Alcohols by a Rhodium(I) Complex

Jun, Chul Ho; Lee, Dae Yon; Kim, Yeon Hee; Lee, Hyuk

doi:10.1021/om010087c

Cited by 53 publications

(22 citation statements)

References 50 publications

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“…This is proposed to be aided by the picoline catalyst 5,w hich can form imine 6 with the ketone substrate (Scheme 4B). [32] 2.3. To favor the formation of the products,anexcess of alkene is typically employed, but the authors also suggest that the styrene by-product can polymerize under the reaction conditions, [28] thereby providing af urther driving force.O verall, this reaction is au seful complement to traditional hydroacylation processes, [29] wherein an alkene inserts directly into an aldehyde,s ince there are cases where the use of the bare aldehyde is unfavorable.F or example,a cetaldehyde can be ac hallenging substrate to work with.…”

Section: Rcho Transfermentioning

confidence: 99%

Catalytic Isofunctional Reactions—Expanding the Repertoire of Shuttle and Metathesis Reactions

2019

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Transfer hydrogenation, alkene metathesis and alkyne metathesis possess great value to the synthetic chemistry community. One of the key features of these processes is their reversibility which can be attributed to the presence of the same number and type of functional groups in both the reactants and products, making these reactions isofunctional. These classic reactions have recently inspired the development of novel shuttle and metathesis reactions that offer great promise for synthetic chemistry. This review describes and systematically categorizes both recent and older examples of shuttle and metathesis reactions other than transfer hydrogenation and alkene/alkyne metathesis.

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Section: Rcho Transfermentioning

confidence: 99%

Catalytic Isofunctional Reactions—Expanding the Repertoire of Shuttle and Metathesis Reactions

2019

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“…In Hinblick auf den Mechanismus wird angenommen, dass der Picolinkatalysator 5 mit dem Ketonsubstrat ein Imin 6 bildet (Schema 4B). [32] Um die Bildung des Produktes zu begünstigen, wird normalerweise das Alken im Überschuss eingesetzt.…”

Section: Rcho-transferunclassified

Katalytische, isofunktionelle Reaktionen – Erweiterung des Repertoires an Shuttle‐ und Metathesereaktionen

Bhawal

Morandi

2019

Angewandte Chemie

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Transferhydrierungsreaktionen, genauso wie Metathesereaktionen von Alkenen und Alkinen, sind von großer Bedeutung in der Synthesechemie. Ein gemeinsames Schlüsselmerkmal dieser Verfahren ist ihre Reversibilität, die davon herrührt, dass sowohl Startverbindungen als auch Produkte die gleiche Anzahl und Art von funktionellen Gruppen aufweisen und die Verfahren somit isofunktionell machen. Diese klassischen Reaktionen trugen in letzter Zeit dazu bei, neuartige Shuttle‐ und Metathesereaktionen zu entwickeln, die vielversprechend für die Synthesechemie sein könnten. Dieser Aufsatz beschreibt und ordnet aktuelle wie auch ältere Beispiele von Shuttle‐ und Metathesereaktionen (mit Ausnahme von Transferhydrierungen und Metathesereaktionen von Alkenen und Alkinen).

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“…In 1999, the Jun group reported as eminal example of CÀC bond activation, and one of the earliest examples of shuttle catalysis, that enables the hydroacylation of alkenes. [8] The authors found that through the co-operativec atalysis of ar hodium catalyst and 2-aminopicoline 1 the hydroacylation of alkenes could be achieved using simple ketonesa sa ldehyde donors (Scheme 2). The driving force for this reactioni sm ost likely polymerization of the styrene by-product although al arge excesso ft he ketone is also used.…”

Section: Forward Shuttle Catalysis For the Functionalization Of Unsatmentioning

confidence: 99%

Shuttle Catalysis—New Strategies in Organic Synthesis

Bhawal

Morandi

2017

Chemistry A European J

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Shuttle catalysis has recently emerged as a powerful new concept that provides a platform for performing both functionalization and defunctionalization reactions. In this concept article, applications of shuttle catalysis as a novel strategy in organic synthesis are discussed. This includes using forward shuttle catalysis reactions for challenging bond-forming processes that avoid the use of hazardous chemicals. Shuttle catalysis also facilitates the transfer of reactive functionality as a route to procure a broad range of compounds using one simple procedure. Reverse shuttle catalysis reactions are also discussed as a method for the valorization of biomass and waste materials. Another area of interest, shuttle-catalysis-assisted reactions, wherein the transfer of a small molecule is utilized in a catalytic cycle, is also described. Possible future directions in this exciting new field are also suggested.

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Catalytic Carbon−Carbon Bond Activation ofsec-Alcohols by a Rhodium(I) Complex

Cited by 53 publications

References 50 publications

Catalytic Isofunctional Reactions—Expanding the Repertoire of Shuttle and Metathesis Reactions

Catalytic Isofunctional Reactions—Expanding the Repertoire of Shuttle and Metathesis Reactions

Katalytische, isofunktionelle Reaktionen – Erweiterung des Repertoires an Shuttle‐ und Metathesereaktionen

Shuttle Catalysis—New Strategies in Organic Synthesis

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