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

Citations Over TimeTop 1% of 2013 papers

Abstract

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.

Related Papers

• → 4.07 Electrophilic Cyclization(2014)16 cited
• → KF/Al₂O₃‐Mediated N‐Alkylation of Amines and Nitrogen Heterocycles and S‐Alkylation of Thiols(2006)22 cited
• → Brønsted acid-assisted N-alkylation of sulfonamides using ethers as the alkylation reagents(2013)9 cited
• → Some reactions of soft electrophiles with esters and other compounds containing the thiocarbonyl group(1976)18 cited
• → Formation of Aldehydes and Ketones by Alkylation of α‐ and β‐Substituted Carbonyl Compounds(2018)