Palladium‐Catalyzed Intermolecular Arylcarbonylation of Unactivated Alkenes: Incorporation of Bulky Aryl Groups at Room Temperature

Li, Xiang; Chen, Pinhong; Liu, Guosheng

doi:10.1002/ange.201810405

Cited by 12 publications

(1 citation statement)

References 70 publications

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“…7 In addition, the priority binding of olefins instead of CO to C–Pd( ii )–X species can be accomplished via the Pd-catalysed intra-molecular Heck cyclisation–carbonylation reaction; however, this reaction usually realises intra-molecular transformations. 8,9…”

Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed multi-component Heck alkynylcarbonylation of unactivated alkenes for synthesis of β,γ-alkynoates

Peng,

Hong,

Wang

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Palladium-catalyzed multi-component Heck alkynylcarbonylation of unactivated alkenes for synthesis of β,γ-alkynoates

Peng,

Hong,

Wang

et al. 2024

Org. Chem. Front.

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Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Brønsted Acid

Ahmed

Zhang

et al. 2019

Angewandte Chemie

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The cooperative catalysis of copper,s ilver,a nd Brønsted acid is presented as an ew strategy for olefin functionalization. The catalytic direct carbohydroxylation of arylalkenes with allylic alcohols provided as traightforward and efficient approach for preparing 4,5-unsaturated alcohols. Synthetically useful functional groups,such as Cl, Br,carbonyl, and chloromethyl, remained intact during the functionalization reaction.The transition metal catalyzed functionalization of olefins is ap owerful tool to convert readily available petrochemical feedstocks into valuable synthetic building blocks. [1] The development of convenient and efficient methods for the functionalization of olefins is still ar esearch hotspot in organic synthesis although many catalytic methods for the mono-and di-functionalization of olefins have been reported over the past years.Many kind of metals,such as palladium, [2] rhodium, [3] gold, [4] nickel, [5] and copper, [6] were employed as the catalysts for this purpose.Direct carbohydroxylation of alkenes,w hich is the addition of C( alkyl and aryl) and OH to alkenes,i sa n important synthetic method for functionalization of the C=C bond. However,tothe best of our knowledge,only few papers on direct carbohydroxylation, namely arylhydroxylation of alkenes,h ave been reported, and they involve ar adical process. [7] Some examples of indirect carbohydroxylation of alkenes are known. [8] In addition, catalytic allylation of olefins,aH eck-type coupling reaction using allylic ethers, [9] allylic carbonates, [9] allylic tosylate, [10] and allylic alcohols [11] as allyl sources have also been reported. However,a sf ar as we know,t here is no precedent of direct addition of allylic alcohols to alkenes using transition-metal catalysts.H erein, we report that aw ide range of arylalkenes react with allylic alcohols under the cooperative catalysis of Cu, Ag, and[*] W. Ahmed, [+] Dr.

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Asymmetric Palladium‐Catalyzed Oxycarbonylation of Terminal Alkenes: Efficient Access to β‐Hydroxy Alkylcarboxylic Acids

Tian

Chen

et al. 2021

Angewandte Chemie

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A novel PdII‐catalyzed enantioselective oxycarbonylation of alkenes has been established. The ligand with an ethyl group at the C‐6 position of Pyox plays a significant role in the intermolecular oxypalladation process, leading to high reactivity and excellent enantioselective control. Compared to the conventional methods, the reaction itself features alkenes as easily prepared starting materials, mild and operationally simple reaction conditions, and insensitivities to air and water. Moreover, this method allows for broad alkene substrate scope, excellent regio‐ and enantioselectivities, scalabilities and a wide array of applications, and provides a useful route for the convenient and straightforward synthesis of chiral β‐hydroxy alkylcarboxylic acids/esters.

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Palladium‐Catalyzed Intermolecular Arylcarbonylation of Unactivated Alkenes: Incorporation of Bulky Aryl Groups at Room Temperature

Cited by 12 publications

References 70 publications

Palladium-catalyzed multi-component Heck alkynylcarbonylation of unactivated alkenes for synthesis of β,γ-alkynoates

Palladium-catalyzed multi-component Heck alkynylcarbonylation of unactivated alkenes for synthesis of β,γ-alkynoates

Direct Carbohydroxylation of Arylalkenes with Allylic Alcohols: Cooperative Catalysis of Copper, Silver, and a Brønsted Acid

Asymmetric Palladium‐Catalyzed Oxycarbonylation of Terminal Alkenes: Efficient Access to β‐Hydroxy Alkylcarboxylic Acids

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