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

doi:10.1055/s-2008-1067208

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

Research output: Contribution to journal › Article › Research › peer-review

13 Citations (Scopus)

Abstract

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 language	English
Article number	P04408SS
Pages (from-to)	2764-2770
Number of pages	7
Journal	Synthesis
Issue number	17
DOIs	https://doi.org/10.1055/s-2008-1067208
Publication status	Published - 2 Sept 2008
Externally published	Yes

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

abstract = "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.",

author = "Lorimer, \{Anna V.\} and O'Connor, \{Patrick D.\} and Brimble, \{Margaret A.\}",

year = "2008",

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doi = "10.1055/s-2008-1067208",

language = "English",

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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 - https://www.scopus.com/pages/publications/51949093230

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DO - 10.1055/s-2008-1067208

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EP - 2770

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JF - Synthesis

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ER -

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

Abstract

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