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Palladium-Catalyzed C–H Activation/Cross-Coupling of Pyridine N‑Oxides with Nonactivated Secondary Alkyl Bromides

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posted on 2013-01-16, 00:00 authored by Bin Xiao, Zhao-Jing Liu, Lei Liu, Yao Fu
An unexpected C–H activation/C–C cross-coupling reaction has been found to occur between pyridine N-oxides and general nonactivated secondary and even tertiary alkyl bromides. It provides a practically useful approach for the synthesis of alkylated pyridine derivatives. Experimental observations indicated that the C–Br cleavage step involves a radical-type process. Thus, the title reaction provides a rather extraordinary example of Pd-catalyzed cross-coupling of secondary and tertiary aliphatic electrophiles.