Directed ortho Metalation-Boronation and Suzuki-Miyaura Cross Coupling of Pyridine Derivatives: A One-Pot Protocol to Substituted Azabiaryls#

M Alessi, AL Larkin, KA Ogilvie, LA Green…

Index: Alessi, Manlio; Larkin, Andrew L.; Ogilvie, Kevin A.; Green, Laine A.; Lai, Sunny; Lopez, Simon; Snieckus, Victor Journal of Organic Chemistry, 2007 , vol. 72, # 5 p. 1588 - 1594

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Citation Number: 96

Abstract

A general method for the synthesis of azabiaryls 19a-t by a one-pot procedure involving a Directed ortho metalation (D o M)-boronation-Suzuki-Miyaura cross coupling sequence is described. Aside from the three isomeric pyridyl carboxamides 15a-c, chloro-, fluoro-, and O- carbamoyl pyridines are adapted to this method providing a range of azabiaryls (Table 2). The method has an advantage in that it avoids the recognized difficult isolation of pyridyl ...