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Volumn 47, Issue 25, 2008, Pages 4695-4698

A general and efficient method for the Suzuki-Miyaura coupling of 2-pyridyl nucleophiles

Author keywords

C C coupling; Nitrogen heterocycles; Palladium; Suzuki Miyaura coupling

Indexed keywords

BROMINE COMPOUNDS; CHEMICAL REACTIONS; NUCLEOPHILES; PALLADIUM;

EID: 48849092532     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801465     Document Type: Article
Times cited : (216)

References (38)
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    • Recent reviews: a
    • Recent reviews: a) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59;
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    • Eds, F. Diederich, A. de Meijere, Wiley-VCH, New York, chap.2
    • c) N. Miyaura in Metal-Catalyzed Cross-Coupling Reaction (Eds.: F. Diederich, A. de Meijere), Wiley-VCH, New York, 2004, chap.2.
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    • Miyaura, N.1
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    • For a review of the Suzuki-Miyaura reaction of heteroaryl nucleophiles, see
    • For a review of the Suzuki-Miyaura reaction of heteroaryl nucleophiles, see: E. Tyrell, P. Brookes, Synthesis 2004, 4, 469-483.
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    • Tyrell, E.1    Brookes, P.2
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    • For examples of Suzuki-Miyaura reactions of 2-pyridyl boronic acids, see: a K. Deshayes, R. D. Broene, I. Chao, C. B. Knobler, F. Diederich, J. Org. Chem. 1991, 56, 6787-6795;
    • For examples of Suzuki-Miyaura reactions of 2-pyridyl boronic acids, see: a) K. Deshayes, R. D. Broene, I. Chao, C. B. Knobler, F. Diederich, J. Org. Chem. 1991, 56, 6787-6795;
  • 17
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    • utilizing 2-pyridyl pinacol boronate esters. Chlorod ialkyl phosphines and dialkyl phosphine oxides were used as supporting ligands
    • During the development of this work, we discovered unpublished results from CombiPhos Catalysts, Inc
    • During the development of this work, we discovered unpublished results from CombiPhos Catalysts, Inc. utilizing 2-pyridyl pinacol boronate esters. Chlorod ialkyl phosphines and dialkyl phosphine oxides were used as supporting ligands. However, we found that 2-pyridyl pinacol boronate ester was not effectively coupled under our conditions as seen in Table 1.
    • However, we found that 2-pyridyl pinacol boronate ester was not effectively coupled under our conditions as seen in Table , vol.1
  • 18
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    • For examples of Suzuki-Miyaura reactions of 2-pyridyl N,N-diethanolamine boronate esters, see: a P. B. Hodgson, F. H. Salingue, Tetrahedron Lett. 2004, 45, 685-687;
    • For examples of Suzuki-Miyaura reactions of 2-pyridyl N,N-diethanolamine boronate esters, see: a) P. B. Hodgson, F. H. Salingue, Tetrahedron Lett. 2004, 45, 685-687;
  • 20
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    • For work with 2-pyridyltrifluoroborates, see
    • For work with 2-pyridyltrifluoroborates, see: G. A. Molander, B. Biolatto, J. Org. Chem. 2003, 68, 4302-4314.
    • (2003) J. Org. Chem , vol.68 , pp. 4302-4314
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    • For selected examples of phosphine oxides ligands in carbon-carbon bond-forming cross-coupling processes, see: a G. Y. Li, Angew. Chem. 2001, 113, 1561-1564;
    • For selected examples of phosphine oxides ligands in carbon-carbon bond-forming cross-coupling processes, see: a) G. Y. Li, Angew. Chem. 2001, 113, 1561-1564;
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    • Substituted Pyridines as Selective Cyclooxygenase-2 Inhibitors: D. Dube, R. Fortin, R. Friesen, Z. Wang, J. Gauthier Merck Frost Canada Inc, WO 98/03484, 1998;
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    • Process for the Production of Quinazolines: B. Ahman, P. Hodgson, S. Lewandowski, R. Walton Pfizer Inc, WO 02/094815, 2002
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    • The 2-pyridylborates are somewhat air-sensitive, so they were stored in a benchtop desiccator to prolong the lifetime of the reagents. However, during the setup of each reaction, these reagents were weighed out on a bench open to the air.
    • The 2-pyridylborates are somewhat air-sensitive, so they were stored in a benchtop desiccator to prolong the lifetime of the reagents. However, during the setup of each reaction, these reagents were weighed out on a bench open to the air.


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