Dehydrative Allylation between Aldehydes and Allylic Alcohols through Synergistic N‐Heterocyclic Carbene/Palladium Catalysis

Haruki, Hiroki; Yasuda, Shigeo; Nagao, Kazunori; Ohmiya, Hirohisa

doi:10.1002/chem.201805955

Cited by 52 publications

(19 citation statements)

References 56 publications

(18 reference statements)

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“…In cases where the allylic electrophile is less reactive, such as allylic acetates or carbonates, allylic alkylations can be performed with the assistance of a catalyst. This latter method has the advantage of more stable electrophilic substrates and has been widely employed with enantioenriched transition-metal catalysts [16][17][18][19][20][21][22][23][24][25] , most notably in the Tsuji-Trost reaction [26][27][28][29][30][31][32] . The shortcoming of this approach is it generally relies on precious metal catalysts.…”

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confidence: 99%

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

et al. 2021

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Allylation of nucleophiles with highly reactive electrophiles like allyl halides can be conducted without metal catalysts. Less reactive electrophiles, such as allyl esters and carbonates, usually require a transition metal catalyst to facilitate the allylation. Herein, we report a unique transition-metal-free allylation strategy with allyl ether electrophiles. Reaction of a host of allyl ethers with 2-azaallyl anions delivers valuable homoallylic amine derivatives (up to 92%), which are significant in the pharmaceutical industry. Interestingly, no deprotonative isomerization or cyclization of the products were observed. The potential synthetic utility and ease of operation is demonstrated by a gram scale telescoped preparation of a homoallylic amine. In addition, mechanistic studies provide insight into these C(sp3)–C(sp3) bond-forming reactions.

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confidence: 99%

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

et al. 2021

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“…In addition, synergistic N ‐heterocyclic carbene (NHC)/Pd catalysis are found highly effective for allylation of aldehydes with different allylic electrophiles including allyl alcohol and allyl amine [111–112] . This significantly broadens the scope of synergistic NHC/Pd catalyzed protocol.…”

Section: Combining N‐heterocyclic Carbenes (Nhc) With Transition Meta...mentioning

confidence: 99%

Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

et al. 2022

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The combination of organocatalysis with transition metal catalysis is an emerging research area for the scientific community. Various unprecedented transformations that are otherwise inaccessible by individual catalytic systems can be achieved with good efficiency and stereocontrolled manner by this dual-catalytic strategy. This Review presents a detailed discussion on the recent advances in dual catalytic systems combining organocatalysis and transition metal catalysis, covering the literature of the last five years. A wide variety of combinations of transition metals with organocatalysts including aminocatalysts, such as secondary amines and more recent primary amines, Brønsted acid catalysts, especially phosphoric acids based on the chiral BINOL scaffold and N-heterocyclic carbene catalysts, are discussed. Considering the great contribution of this domain to organic synthesis, the present and future potential of this new and exciting research field is highlighted.

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“…β,γ-unsaturated ketones are not only versatile synthons but also prominent motifs in pharmaceuticals and natural products. [54] In general,β,γ-unsaturated ketones are produced by the acylation of olefins, which may also generate conjugated α,β-unsaturated ketones as a side product due to prototropic rearrangement. [55] Under this purview, nano copper ferritehas been employed by Murthy etal.…”

Section: Synthesis Of βγ-Unsaturated Ketonesmentioning

confidence: 99%

Synthesis and Reactivity of Copper and Copper Containing Magnetically Separable Catalysts

Kundu

Mondal

Das³

et al. 2022

ChemistrySelect

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This review endeavours to summarize the emergence of magnetically separable catalysts as a new class of catalyst for the modern developments in the synthesis and reactivity of the nano‐sized magnetically separable copper and copper containing nanomaterials exploited as potent applicant in the field of material science not only for their widespread technological applications but also to realize the fundamentals of nano‐magnetism. This review covers extensively different catalytic reactivity for carbon‐carbon and carbon‐heteroatom bond formation reactions and emphasized on recent developments in the field.

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Dehydrative Allylation between Aldehydes and Allylic Alcohols through Synergistic N‐Heterocyclic Carbene/Palladium Catalysis

Abstract: Dehydrative allylation between widely available aldehydes and allylic alcohols to afford β,γ‐unsaturated ketones was enabled by a synergistic merger of a thiazolium N‐heterocyclic carbene catalyst and a palladium‐bisphosphine catalyst.

Cited by 52 publications

References 56 publications

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms

Combined Power of Organo‐ and Transition Metal Catalysis in Organic Synthesis

Synthesis and Reactivity of Copper and Copper Containing Magnetically Separable Catalysts

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