A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles

Angewandte Chemie - International Edition

Volumn 45, Issue 8, 2006, Pages 1282-1284

  Kudo, Noriaki ^a   Perseghini, Mauro ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cross coupling; Heterocycles; Homogeneous catalysis; Nitrogen; Palladium

Indexed keywords

BORONATE ESTERS; CROSS-COUPLING; HETEROCYCLES; HOMOGENEOUS CATALYSIS;

ACETONE; BENZENE; BORON COMPOUNDS; CHEMICAL ACTIVATION; CHLORINE COMPOUNDS; ESTERS; HYDROXYLATION; PALLADIUM; REACTION KINETICS; SUBSTITUTION REACTIONS; SUBSTRATES;

NITROGEN COMPOUNDS;

BORONIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

BORONIC ACIDS; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; NITROGEN;

EID: 33745721269     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503479     Document Type: Article

References (18)

1. For leading references, see: a) N. Miyaura in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, New York, 2004, chap. 2;
2. b) A. Suzuki in Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E.-i. Negishi), Wiley Interscience, New York, 2002, chap. III.2.2.
3. For an overview, see: A. M. Rouhi, Chem. Eng. News 2004, 82, 49-58.
4. For recent reports that include Suzuki reactions of nitrogen heterocycles, see: a) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696;
5. b) T. E. Barder, S. L. Buchwald, Org. Lett. 2004, 6, 2649-2652;
6. c) I. Kondolff, H. Doucet, M. Santelli, Synlett 2005, 2057-2061;
7. d) A. E. Thompson, G. Hughes, A. S. Batsanov, M. R. Bryce, P. R. Parry, B. Tarbit, J. Org. Chem. 2005, 70, 388-390, and references therein.
8. a) For a discussion of the widespread occurrence of nitrogen heterocycles, particularly pyridines, in pharmaceutically active compounds, see: V. Bonnet, F. Mongin, F. Trecourt, G. Breton, F. Marsais, P. Knochel, G. Queguiner, Synlett 2002, 1008-1010 (footnote 1);
9. b) A. F. Pozharskii, A. T. Soldartenko, A. Katritzky, Heterocycles in Life and Society, Wiley, New York, 1997.
10. For an overview, see: J. Tsuji, Palladium Reagents and Catalysts, Wiley, New York, 2004.
11. A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028;
12. see, also: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587;
13. Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
14. 3 for palladium-catalyzed Suzuki reactions, see: W. Shen, Tetrahedron Lett. 1997, 55, 5575-5578.
15. For an overview of the use of water as a (co)solvent for Suzuki reactions, see: N. E. Leadbeater, Chem. Commun. 2005, 2881-2902.
16. For the application of a related system to the cross-coupling of cyclopropylboronic acid with (hetero)aryl bromides, see: D. J. Wallace, C.-y. Chen, Tetrahedron Lett. 2002, 43, 6987-6990.
17. For the Suzuki cross-coupling illustrated in entry 15 of Table 1, deboronation is a significant side reaction.
18. For a previous example, see: C. N. Johnson, G. Stemp, N. Anand, S. C. Stephen, T. Gallagher, Synlett 1998, 1025-1027.