Ligand-dependent site-selective suzuki cross-coupling of 3,5-dichloropyridazines

Journal of Organic Chemistry

Volumn 78, Issue 15, 2013, Pages 7758-7763

  Dai, Xing ^a   Chen, Yonggang ^a   Garrell, Stephanie ^a   Liu, Hong ^a   Zhang, Li Kang ^a   Palani, Anandan ^a   Hughes, Gregory ^a   Nargund, Ravi ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GENERAL METHOD; HIGH SELECTIVITY; RAPID CONSTRUCTION; SITE SELECTIVE; SUZUKI CROSS COUPLING;

EXCITONS;

LIGANDS;

BENZENEBORONIC ACID; LIGAND; PYRIDAZINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; ELECTRON; SUZUKI REACTION; TEMPERATURE;

EID: 84881251682     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401096u     Document Type: Article

References (18)

1. Rossi, R.; Bellina, F.; Lessi, M. Adv. Synth. Catal. 2012, 354, 1181
2. Rossi, R.; Bellina, F.; Lessi, M. Tetrahedron 2011, 67, 6969
3. Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036
4. Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245
5. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020
6. Claremon, D. A.; Zhuang, L.; Leftheris, K.; Tice, C. M.; Xu, Z.; Ye, Y.; Singh, S. B.; Cacatian, S.; Zhao, W.; Himmelsbach, F.; Eckhardt, M. Patent WO 2009134392, 2009.
7. Houpis, I. N.; Liu, R.; Wu, Y.; Yuan, Y.; Wang, Y.; Nettekoven, U. J. Org. Chem. 2010, 75, 6965
8. Yang, W.; Wang, Y.; Corte, J. R. Org. Lett. 2003, 5, 3131
9. Houpis, I. N.; Huang, C.; Nettekoven, U.; Chen, J. G.; Liu, R.; Canters, M. Org. Lett. 2008, 10, 5601
10. Strotman, N. A.; Chobanian, H. R.; He, J.; Guo, Y.; Dormer, P. G.; Jones, C. M.; Steves, J. E. J. Org. Chem. 2010, 75, 1733
11. Garcia, Y.; Schoenebeck, F.; Legault, C. Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 6632
12. Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664
13. Herrebout, W. A.; Nagels, N.; Verbeeck, S.; van der Veken, B. J.; Maes, B. U. W. Eur. J. Org. Chem. 2010, 3152
14. Handy, S. T.; Zhang, Y. Chem. Commun. 2006, 299
15. 3 is not bi-dentate. For reference of the second-generation biphenyl pre-catalyst please see: Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073
16. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 10718
17. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. J. Org. Chem. 2002, 67, 5553
18. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 2008, 47, 6338