Direct Palladium‐Catalyzed C5‐Arylation of 1,3,4‐Oxadiazoles with Aryl Chlorides Promoted by Bis(diisopropylphosphino)ferrocene
European Journal of Organic Chemistry(2024)
摘要
The direct palladium‐catalyzed C–H arylation of 1,3,4‐oxadiazoles with challenging aryl chloride substrates is promoted by the use of a specifically designed electron‐rich ferrocenyl diphosphane. This protocol employs 0.5 to 1.0 mol% catalyst loading without any additives such as copper or ammonium salts, and equally tolerates electron‐donating and electron‐withdrawing substituents on the (heteroaryl)aryl halides, as illustrated by the efficient synthesis in 86% yield of the anti‐tubercular agent PHOXPY (2‐(5‐phenyl‐1,3,4‐oxadiazol‐2‐yl)pyrazine) from a late‐stage arylation using 2‐chloropyrazine.
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