Yb[N(SO2C8F17)2]3-catalyzed allylation of 1,3-dicarbonyl compounds with allylic alcohols in a fluorous biphase system

Shen, Minggui; Cai, Chun; Yi, Wen‐Bin

doi:10.1016/j.jfluchem.2009.03.006

Cited by 12 publications

(3 citation statements)

References 27 publications

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“…Metals featured in early reports in this field include bismuth, , cerium, , ruthenium, , niobium, ytterbium, − molybdenum, − tungsten, scandium, − aluminum, and gold . Indium catalysis has proven common in these deoxygenative functionalization reactions, − as has iron catalysis, particularly utilizing FeCl 3 and its hydrated analogs. − …”

Section: Deoxygenative Functionalizationmentioning

confidence: 99%

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Cook,

Newman

2024

Chem. Rev.

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Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods for their functionalization require them to first be converted into a more activated derivative, while recent years have seen a vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can be used toward this goal. These transformations are broadly classified into three categories. Deoxygenative functionalizations, representing derivatization of the C−O bond, enable the alcohol to act as a leaving group toward the formation of new C−C bonds. Etherifications, characterized by derivatization of the O−H bond, represent classical reactivity that has been modernized to include mild reaction conditions, diverse reaction partners, and high selectivities. Lastly, chain functionalization reactions are described, wherein the alcohol group acts as a mediator in formal C−H functionalization reactions of the alkyl backbone. Each of these three classes of transformation will be discussed in context of intermolecular arylation, alkylation, and related reactions, illustrating how catalysis can enable alcohols to be directly harnessed for organic synthesis.

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Section: Deoxygenative Functionalizationmentioning

confidence: 99%

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Cook,

Newman

2024

Chem. Rev.

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“…Hf, Yb, Sc) complexes with bis(perfluorooctanesulfonyl)imide ponytails are active and recyclable catalysts which could be immobilized in the fluorous phase for synthesis of substituted quinolines [16] and 14-substituted-14H-dibenzo[a,j] xanthenes [17] and allylation of 1,3-dicarbonyl compounds [18]. As part of a continuing effort in our laboratory toward the development of lanthanide complexes catalysts for fluorous phase organic synthesis [19], we present our results about a hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed four-component Hantzsch reaction in fluorous medium.…”

Section: Introductionmentioning

confidence: 99%

Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium

Hong

Cai

2010

Journal of Fluorine Chemistry

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109

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“…Recently, the value of the fluorous phase-separation and fluorous catalyst recyclability under fluorous biphase system (FBS) has been recognised. 20 We have introduced Yb(NPf 2 ) 3 as an efficient Lewis acid catalyst for the allylation of 1,3-dicarbonyl compounds 21 in FBS. A key factor to accomplish the catalytic processes was was believed to be the use of a sufficiently long perfluorinated ligand -N(SO 2 C 8 F 17 ) 2 , whose structural characteristic can coordinate with a variety of metal cations to obtain the desired Lewis acid catalysts with appropriate catalytic activity, as well as the selective immobilisation in the fluorous phase.…”

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confidence: 99%

Ytterbium(III) Bis(Perfluorooctanesulfonyl)Imide Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]Pyrans in Fluorous Biphase System

Cai

2010

Journal of Chemical Research

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Ytterbium(III) bis(perfluorooctanesulfonyl)imide [Yb(NPf 2 ) 3 ] has been prepared, and used as an efficient catalyst for the synthesis of 4H-benzo[b]pyran derivatives by a one-pot three-component condensation of aldehydes, active methylene compounds, and dimedone in a fluorous biphase system (FBS). The reaction proceeds smoothly and affords the corresponding 4H-benzo [b]pyrans in moderate to excellent yields. The catalyst is selectively dissolved in the fluorous phase, can be recovered simply by phase separation and reused several times without any obvious decrease of activity.

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Yb[N(SO2C8F17)2]3-catalyzed allylation of 1,3-dicarbonyl compounds with allylic alcohols in a fluorous biphase system

Cited by 12 publications

References 27 publications

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions

Hafnium (IV) bis(perfluorooctanesulfonyl)imide complex catalyzed synthesis of polyhydroquinoline derivatives via unsymmetrical Hantzsch reaction in fluorous medium

Ytterbium(III) Bis(Perfluorooctanesulfonyl)Imide Catalyzed One-Pot Synthesis of Tetrahydrobenzo[b]Pyrans in Fluorous Biphase System

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