Heck reaction with an acyl synthon: new coupling reaction between α-halo vinyl ether and alkene

Gao, Xiaobang; Yu, Wei; Yan, Mi; Jin, Zhendong

doi:10.1016/j.tetlet.2004.09.029

Tetrahedron Letters

2004

DOI: 10.1016/j.tetlet.2004.09.029

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Heck reaction with an acyl synthon: new coupling reaction between α-halo vinyl ether and alkene

Xiaobang Gao

Wei Yu

Mi Yan

et al.

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Cited by 4 publications

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“…The lithiation of bromine 7 by n -BuLi followed by carboxylation with CO 2 afforded the carboxylic acid 9 in a modest but nonoptimized yield of 27%. In addition, the palladium-catalyzed Heck vinylation of iodide 6 by diethyl allylmalonate (Pd(PPh 3 ) 4 , TEA, DMF) provided 10 in 52% yield . Compound 10 is a very versatile compound as one carboxylate group can be used to introduce a water-soluble moiety while the other can be used to introduce a protein ligand.…”

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confidence: 99%

Scalable Synthesis of Cryptophane-1.1.1 and its Functionalization

et al. 2010

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Cryptophanes, cage molecules for which xenon exhibits a high affinity, are good candidates for xenon biosensing. Cryptophane-1.1.1 (1) exhibits the highest binding constant for xenon encapsulation in organic solution determined to date. This property suggests that the cryptophane-1.1.1 core (1) is optimal for sensing applications. A high-yielding scalable synthesis of compound 1 is reported as well as an easy way to functionalize it.

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Scalable Synthesis of Cryptophane-1.1.1 and its Functionalization

et al. 2010

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Synthesis via α‐Halo Vinyl Ethers. Part 5. Heck Reaction with an Acyl Synthon: New Coupling Reaction Between α‐Halo Vinyl Ether and Alkene.

Gao

Yan

et al. 2005

ChemInform

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Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies

Simić

Paunović

Borić

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Heck reaction with an acyl synthon: new coupling reaction between α-halo vinyl ether and alkene

Cited by 4 publications

References 23 publications

Scalable Synthesis of Cryptophane-1.1.1 and its Functionalization

Scalable Synthesis of Cryptophane-1.1.1 and its Functionalization

Synthesis via α‐Halo Vinyl Ethers. Part 5. Heck Reaction with an Acyl Synthon: New Coupling Reaction Between α‐Halo Vinyl Ether and Alkene.

Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies

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