Palladium-Catalyzed Arylation of Unactivated γ-Methylene C(sp3)H and δ-CH Bonds with an Oxazoline-Carboxylate Auxiliary

A palladium‐catalyzed arylation of unactivated γ‐methylene C(sp3)H and remote δ‐CH bonds by using an oxazoline‐carboxylate directing group has been developed. Arylation occurs with a broad substrate scope and high tolerance of functional groups (i.e., halogen, nitro, cyano, ether, trifluoromethyl,...

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Veröffentlicht in:Chemistry : a European journal 2015-11, Vol.21 (48), p.17503-17507
Hauptverfasser: Ling, Peng-Xiang, Fang, Sheng-Long, Yin, Xue-Song, Chen, Kai, Sun, Bo-Zheng, Shi, Bing-Feng
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Sprache:eng
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Zusammenfassung:A palladium‐catalyzed arylation of unactivated γ‐methylene C(sp3)H and remote δ‐CH bonds by using an oxazoline‐carboxylate directing group has been developed. Arylation occurs with a broad substrate scope and high tolerance of functional groups (i.e., halogen, nitro, cyano, ether, trifluoromethyl, amine, and ester). The oxazoline‐type auxiliary can be removed under acidic conditions. Active construction: A palladium‐catalyzed arylation of unactivated γ‐methylene C(sp3)H and remote δ‐CH bonds is accomplished by using an oxazoline‐carboxylate directing group (see scheme). Arylation occurs with a broad substrate scope and high tolerance of functional groups (i.e., halogen, nitro, cyano, ether, trifluoromethyl, amine, and ester). The oxazoline‐type auxiliary can be removed under acidic conditions.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502621