Synthesis and crystal structures of palladium complexes based on <mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mi>α</mml:mi></mml:math>-amino-oximes derived from (<mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML"><mml:mi>R</mml:mi></mml:math>)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Homrani, Yasmina; Amrani, Mohamed Amin El; Loxq, Pauline; Capet, Frédéric; Suisse, Isabelle; Sauthier, Mathieu

doi:10.5802/crchim.142

Comptes Rendus. Chimie

2022

DOI: 10.5802/crchim.142

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Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Yasmina Homrani¹,

Mohamed Amin El Amrani²,

Pauline Loxq³

et al.

Abstract: Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

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2024

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Cited by 3 publications

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Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Kokina,

Shekhovtsov,

Tkachev

et al. 2024

ChemPlusChem

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The first example of the palladium‐catalyzed sp3 C‐H bond activation in a monoterpene‐based compound has been observed in the reaction of PdCl2 with a (+)‐3‐carene‐based ligand HL (HL = N‐((1aS,3S,7bR)‐1,1,3‐trimethyl‐7‐phenyl‐5‐(pyridin‐2‐yl)‐1a,2,3,7b‐tetrahydro‐1H‐cyclopropa[f]quinolin‐3‐yl)acetamide), which yielded the [PdLCl] complex. In contrast to the vast majority of C(sp3)‐H activation reactions which require prolonged heating and mixing due to the inert character of the corresponding bond, the reaction reported herein proceeds rapidly under mild conditions. A theoretical insight into the ligand deprotonation has been performed by DFT calculations. The mechanism of the C‐H activation involves (i) simultaneous coordination of the CH3 group of HL to the Pd2+ ion and decoordination of the Cl‐ anion with consequent formation of a Cl⋅⋅⋅H‐N hydrogen bond with the amide group, (ii) approximation of the out‐of‐sphere Cl‐ anion to one of the hydrogen atoms of the CH3 group mediated by the crane motion of the amide group and (iii) the ejection of the HCl molecule, which increases the entropy of the system and serves as a driving force for the reaction.

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Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Kokina,

Shekhovtsov,

Tkachev

et al. 2024

ChemPlusChem

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show abstract

Copper(II), zinc(II) and cadmium(II) complexes with the O-picolyl ether of chiral α-aminooxime of natural (+)-limonene: synthesis, structures, luminescence and cytotoxicity

Kokina,

Agafontsev,

Shekhovtsov

et al. 2024

Inorganic Chemistry Communications

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Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III)

Tkachev,

Agafontsev,

Zubricheva

et al. 2024

Tetrahedron

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Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Abstract: Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Cited by 3 publications

References 25 publications

Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Copper(II), zinc(II) and cadmium(II) complexes with the O-picolyl ether of chiral α-aminooxime of natural (+)-limonene: synthesis, structures, luminescence and cytotoxicity

Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III)

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Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Abstract: Synthesis and crystal structures of palladium complexes based on α-amino-oximes derived from (R)-limonene and their application in allylic alkylation of 1,3-dioxo compounds

Cited by 3 publications

References 25 publications

Palladium‐Catalyzed C(sp3)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Palladium‐Catalyzed C(sp3)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Copper(II), zinc(II) and cadmium(II) complexes with the O-picolyl ether of chiral α-aminooxime of natural (+)-limonene: synthesis, structures, luminescence and cytotoxicity

Chiral hybrid aza-oxa-terpene-based macrocycles as selective extractants for Pd(II) and Au(III)

Contact Info

Product

Resources

About

Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study

Palladium‐Catalyzed C(sp³)−H Activation in A Monoterpene‐Based Compound Under Mild Conditions: A Combined Experimental and Theoretical Mechanistic Study