Asymmetric Suzuki–Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover

Asymmetric Suzuki–Miyaura reaction proceeded in 5 h with 0.1 mol % catalyst loading, giving 75% yield and 76% ee. A series of new chiral phosphonite ligands were evaluated for the palladium-catalyzed asymmetric Suzuki–Miyaura cross-coupling reactions of aryl chlorides. Ligand 4 gave 91% yield and 78...

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Published inTetrahedron letters Vol. 52; no. 21; pp. 2638 - 2641
Main Authors Kamei, Toshinori, Sato, Akihiro H., Iwasawa, Tetsuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.05.2011
Elsevier
Subjects
Aromatic compounds
Asymmetry
Catalysts
Chemical reactions
Chemistry
Chemistry, Organic
Chlorides
Joining
Ligands
Physical Sciences
Science & Technology
Tetrahedrons
ROUTE
LIGANDS
COMPLEXES
SCIENCE
CHIRALITY
DERIVATIVES
BIARYLS
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Summary:Asymmetric Suzuki–Miyaura reaction proceeded in 5 h with 0.1 mol % catalyst loading, giving 75% yield and 76% ee. A series of new chiral phosphonite ligands were evaluated for the palladium-catalyzed asymmetric Suzuki–Miyaura cross-coupling reactions of aryl chlorides. Ligand 4 gave 91% yield and 78% ee with 0.5 mol % catalyst loading for the coupling of aryl boronic acid and aryl chloride in 5 h. When the catalyst loading was lowered to 0.1 mol % the same reaction gave 75% yield and 76% ee.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.03.051