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Regioselective Direct C-3 Arylation of Imidazo[1,2-a]pyridines with Aryl Tosylates and Mesylates Promoted by Palladium–Phosphine Complexes

Author:
Choy, Pui Ying, Luk, Kwan Chak, Wu, Yinuo, So, Chau Ming, Wang, Lai-lai, Kwong, Fuk Yee
Source:
Journal of organic chemistry 2015 v.80 no.3 pp. 1457-1463
ISSN:
1520-6904
Subject:
Lewis acids, acetates, aromatic hydrocarbons, arylation, catalysts, chemical structure, organic chemistry, palladium, pyridines, regioselectivity, sulfonates
Abstract:
Direct C-3 arylation of imidazo[1,2-a]pyridines with aryl tosylates and mesylates has been accomplished by employing palladium(II) acetate associated with SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) or L1 (2-(2-(diisopropylphosphino)phenyl)-1-methyl-1H-indole). This catalyst system can be applied to a wide range of aryl sulfonates and shows excellent C-3 regioselectivity of imidazo[1,2-a]pyridine. These results represent the first examples of using tosylate- and mesylate-functionalized arenes as the electrophile partners for this regioselective direct arylation.
Agid:
5505036