TY - JOUR
T1 - Buchwald-Hartwig Mono-N-arylation with 2,6-dihaloisonicotinic acid derivatives
T2 - A convenient desymmetrization method
AU - Lorimer, Anna V.
AU - O'Connor, Patrick D.
AU - Brimble, Margaret A.
PY - 2008/9/2
Y1 - 2008/9/2
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=51949093230&partnerID=8YFLogxK
U2 - 10.1055/s-2008-1067208
DO - 10.1055/s-2008-1067208
M3 - Article
AN - SCOPUS:51949093230
SN - 0039-7881
SP - 2764
EP - 2770
JO - Synthesis
JF - Synthesis
IS - 17
M1 - P04408SS
ER -