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Photoredox-catalysed regioselective synthesis of C-4-alkylated pyridines with N-(acyloxy)phthalimides. 2022
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China. xiaofeizhang@simm.ac.cn.
A method of direct C-4 selective alkylation of pyridines under visible light irradiation at room temperature has been reported, using simple maleate-derived pyridinium salts as pyridine precursors and the readily available carboxylic acid-derived N-(acyloxy)phthalimides as alkyl radical precursors, affording good to excellent yields without using stoichiometric oxidants and acids. A broad range of primary, secondary, and tertiary carboxylates can be used as alkylation reagents. Oxidant and acid-sensitive functional groups can be tolerated well.
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