Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Yeh, Ming Chang P.; Jou, Chi Fen; Yeh, Wei Tzou; Chiu, Da Yu; Reddy, N. Ravi Kumar

doi:10.1016/j.tet.2004.10.078

Tetrahedron

2005

DOI: 10.1016/j.tet.2004.10.078

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Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Ming Chang P. Yeh

Chi Fen Jou

Wei Tzou Yeh

et al.

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Cited by 15 publications

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“…Therefore, the construction of a Δ 2 -isoxazoline ring has received much attention. The conventional method for their synthesis is via cycloaddition of nitrile oxides and alkenes, which generates the O−C5 and C3−C4 bond in one step (). , Although these transformations are widely used, some challenges still remain especially for the issue of the regioselectivity …”

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Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

2008

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A novel route to the synthesis of Delta2-isoxazoline derivatives is described. Reaction of beta,gamma-unsaturated oximes with aryl bromides via palladium-catalyzed carboetherification affords 3,5-disubstituted Delta2-isoxazolines in good yields. The use of Xantphos as ligand is crucial for the transformation. The carboetherification products can be further converted to beta-hydroxy ketones in the presence of Fe powder and NH4Cl.

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Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

2008

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Novel (N‐heterocyclic carbene)Pd(pyridine)Br₂ complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes

Ibrahim

Malik

Mansour

et al. 2018

Applied Organom Chemis

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New N,N′-substituted imidazolium salts and their corresponding dibromidopyridine-palladium(II) complexes were successfully synthesized and characterized. Reactions of palladium bromide with the newly synthesized N,N′-substituted imidazolium bromides (2a and 2b) in pyridine afforded the corresponding new N-heterocyclic carbene pyridine palladium(II) complexes (3a and 3b) in high yields. Their single-crystal X-ray structures show a distorted square planar geometry with the carbene and pyridine ligands in trans position. Both complexes show a high catalytic activity in carbonylative Sonogashira coupling reactions of aryl iodides and aryl diiodides with arylalkynes, alkylalkynes and dialkynes.

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Intramolecular 1,3‐Dipolar Cycloaddition of Cyclo‐1,3‐diene‐tethered Nitrile Oxides.

Yeh¹,

Jou²,

Yeh³

et al. 2005

ChemInform

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Isoxazole derivatives R 0240Intramolecular 1,3-Dipolar Cycloaddition of Cyclo-1,3-diene-tethered Nitrile Oxides. -Nitrile oxides are generated in situ from the corresponding cyclohexadienyl, cycloheptadienyl, or cycloheptatrienyl aldoximes by sequential treatment with either BuLi/NCS or Et3N/NCS. They undergo intramolecular cycloaddition reaction to give tricycle-fused isoxazolines in a diastereoselective fashion. -(YEH*, M.-C. P.; JOU, C.-F.; YEH, W.-T.; CHIU, D.-Y.; REDDY, N. R. K.; Tetrahedron 61 (2005) 2, 493-500; Dep. Chem., Natl. Taiwan Norm. Univ., Taipei 117, Taiwan; Eng.) -Klein 22-124

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Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Cited by 15 publications

References 23 publications

Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

Novel (N‐heterocyclic carbene)Pd(pyridine)Br₂ complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes

Intramolecular 1,3‐Dipolar Cycloaddition of Cyclo‐1,3‐diene‐tethered Nitrile Oxides.

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Intramolecular 1,3-dipolar cycloaddition of cyclo-1,3-diene-tethered nitrile oxides

Cited by 15 publications

References 23 publications

Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ2-Isoxazolines

Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ2-Isoxazolines

Novel (N‐heterocyclic carbene)Pd(pyridine)Br2 complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes

Intramolecular 1,3‐Dipolar Cycloaddition of Cyclo‐1,3‐diene‐tethered Nitrile Oxides.

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Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

Pd-Catalyzed Carboetherification of β,γ-Unsaturated Oximes: A Novel Approach to Δ²-Isoxazolines

Novel (N‐heterocyclic carbene)Pd(pyridine)Br₂ complexes for carbonylative Sonogashira coupling reactions: Catalytic efficiency and scope for arylalkynes, alkylalkynes and dialkynes