New catalysts for Suzuki-Miyaura coupling reactions of heteroatom- substituted heteroaryl chlorides

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5104-5112

  Guram, Anil S ^a   Wang, Xiang ^a   Bunel, Emilio E ^a   Faul, Margaret M ^a   Larsen, Robert D ^a   Martinelli, Michael J ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROARYL CHLORIDES; HETEROATOM; SUZUKI-MIYAURA COUPLING REACTIONS;

CATALYSTS; CHLORINE COMPOUNDS; ORGANIC ACIDS; SUBSTITUTION REACTIONS;

REACTION KINETICS;

BORONIC ACID DERIVATIVE; CHLORINE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; COMPLEX FORMATION; REACTION ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 34447307124     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070341w     Document Type: Article

References (47)

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25. Recently, others and we have communicated the development of catalysts and conditions for more general and efficient Suzuki-Miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides; see: (a) Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282-1284.
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39. 2Ph ligand used in the preparation of complex B′ was purchased from Aldrich Chemical Co. and used as such. The complex B was also prepared as shown in Scheme 1. For alternate synthesis of complex B, see ref 9.
40. 1H NMR and IR data, see ref 9.
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43. The catalyst TONs were investigated under otherwise typical reaction conditions without further optimizations. For experiments with heteroaryl boronic acids, 0.1 mol % catalyst E was employed, and the TONs were determined from calibrated HPLC product area %.
44. 2(biphenyl) ligands.
45. 3 catalysts for general Suzuki-Miyaura coupling reactions, see: (a) Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578.
46. (b) Wallace, D. J.; Chen, C. Y. Tetrahedron Lett. 2002, 43, 6987-6990.
47. 2", respectively.