Deprotonative Metalation of Chloro??and Bromopyridines Using Amido??Based Bimetallic Species and Regioselectivity??Computed CH Acidity Relationships

…, TT Nguyen, N Marquise, YS Halauko…

Index: Snegaroff, Katia; Nguyen, Tan Tai; Marquise, Nada; Halauko, Yury S.; Harford, Philip J.; Roisnel, Thierry; Matulis, Vadim E.; Ivashkevich, Oleg A.; Chevallier, Floris; Wheatley, Andrew E. H.; Gros, Philippe C.; Mongin, Florence Chemistry - A European Journal, 2011 , vol. 17, # 47 p. 13284 - 13297

Full Text: HTML

Citation Number: 41

Abstract

Abstract A series of chloro-and bromopyridines have been deprotometalated by using a range of 2, 2, 6, 6-tetramethylpiperidino-based mixed lithium–metal combinations. Whereas lithium–zinc and lithium–cadmium bases afforded different mono-and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium–copper combination, as demonstrated by subsequent trapping with ...