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Pd-Catalyzed Regioselective and Stereospecific Suzuki–Miyaura Coupling of Allylic Carbonates with Arylboronic Acids
- Li, Chenguang, Xing, Juxiang, Zhao, Jingming, Huynh, Patrick, Zhang, Wanbin, Jiang, Pingkai, Zhang, Yong Jian
- Organic letters 2012 v.14 no.1 pp. 390-393
- Suzuki reaction, acids, carbonates, catalytic activity, chemical structure, organic compounds, palladium, regioselectivity, solvents, stereochemistry
- The Pd-catalyzed Suzuki–Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids has been developed in a wet solvent under a base-free system to afford allyl–aryl coupling products in a high level of isolated yields with complete regio- and E/Z-selectivities with good to excellent chemoselectivities. The coupling reaction of optically active allyl carbonates gave allyl–aryl coupling products with excellent enantioselectivities with inversion of the stereochemistry. This coupling method was successfully applied to the synthesis of (S)-naproxen.