Direct ortho-Arylation of Pyridinecarboxylic Acids: Overcoming the Deactivating Effect of sp2-Nitrogen

Research output: Contribution to journalArticle

  • Authors:
  • Adam Johnston
  • Kenneth Ling
  • David Sale
  • Nathalie Lebrasseur
  • Igor Larrosa

Abstract

Direct arylations of pyridines are challenging transformations due to the high Lewis basicity of the sp2-nitrogen. The use of carboxylates as directing groups is reported, facilitating the Pd-catalyzed C–H arylation of this difficult class of substrates. This methodology allows regioselective C3/C4 arylation, without the need to use solvent quantities of the pyridine, and using low-cost chloro- and bromoarenes as coupling partners. Furthermore, carboxylates could be employed as traceless directing groups through a one-pot C–H arylation/Cu(I)-mediated decarboxylation sequence, thereby accessing directing-group-free pyridine biaryls.

Bibliographical metadata

Original languageEnglish
Pages (from-to)6094-6097
Number of pages4
JournalOrganic letters
Volume18
Issue number23
Early online date18 Nov 2016
DOIs
StatePublished - 2 Dec 2016