Synthesis of 1,4-enynes <i>via</i> nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents

He, Xueyi; Wang, Zhong‐Xia

doi:10.1039/d1cc05221g

Cited by 6 publications

(2 citation statements)

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“…This work was extended in 2021 by the same group toward the alkynylation of allyl alcohols using alkynyl zincs to form 1,4-enynes (Scheme 24b). 177 Stoichiometric amounts of MeZnCl were again required, forming zinc alkoxides in situ as reactive intermediates.…”

Section: π-Activated Alcohols Withmentioning

confidence: 99%

“…The reaction was not inhibited in the presence of radical traps, leading the authors to propose a nickel(0)/nickel(II) catalytic cycle rather than a radical pathway. This work was extended in 2021 by the same group toward the alkynylation of allyl alcohols using alkynyl zincs to form 1,4-enynes (Scheme b) . Stoichiometric amounts of MeZnCl were again required, forming zinc alkoxides in situ as reactive intermediates.…”

Section: Deoxygenative Functionalizationmentioning

confidence: 99%

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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: π-Activated Alcohols Withmentioning

confidence: 99%

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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Carbonylative Cross‐Coupling Reaction of Allylic Alcohols and Organoalanes with 1 atm CO Enabled by Nickel Catalysis

Wang

et al. 2022

Angewandte Chemie

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A nickel‐catalyzed three‐component carbonylative cross‐coupling reaction of allylic alcohols and organoalanes with CO at atmospheric pressure is reported, enabling the expedient formation of β,γ‐unsaturated ketones with broad scope. Particularly, the chemoselective allylic carbonylation of diols further highlights the practicability of this protocol. The leverage of organoalanes as both the coupling components and the activators for the alcohol functionalization is crucial for this method, thus no extraneous activators are required.

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Carbonylative Cross‐Coupling Reaction of Allylic Alcohols and Organoalanes with 1 atm CO Enabled by Nickel Catalysis

Wang

et al. 2022

Angew Chem Int Ed

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Synthesis of 1,4-enynes via nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents

Abstract: Nickel-catalyzed cross-coupling of allylic alcohols with alkynylzinc reagents was developed to achieve 1,4-enynes. The protocol exhibits high regio- and E/Z-selectivity, suits for a wide scope of substrates, and tolerates a...

Cited by 6 publications

References 50 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

Carbonylative Cross‐Coupling Reaction of Allylic Alcohols and Organoalanes with 1 atm CO Enabled by Nickel Catalysis

Carbonylative Cross‐Coupling Reaction of Allylic Alcohols and Organoalanes with 1 atm CO Enabled by Nickel Catalysis

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