Buchwald-Hartwig Mono-N-arylation with 2,6-dihaloisonicotinic acid derivatives: A convenient desymmetrization method

Anna V. Lorimer, Patrick D. O'Connor, Margaret A. Brimble

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9 Citations (Scopus)


A method for the Buchwald-Hartwig mono-N-arylation of aniline with methyl 2,6-dichloroisonicotinate using Pd(OAc)2, XPhos, and t-BuONa is reported. Use of m-anisidine under the same conditions resulted in the amidation of the methyl ester. Mono-N-arylation of m-anisidine with 2,6-dichloro-N,N- diisopropylisonicotinamide and 2,6-dibromo-N,N-diisopropylisonicotinamide, however, was successfully achieved using Pd(OAc)2/XPhos/t-BuONa or Pd(OAc)2/(±)-BINAP/K2CO3, respectively. The present study demonstrates the sensitivity of this cross-coupling method to both the steric and electronic nature of the coupling partners.

Original languageEnglish
Article numberP04408SS
Pages (from-to)2764-2770
Number of pages7
Issue number17
Publication statusPublished - 2 Sep 2008
Externally publishedYes


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