Copper-catalyzed aromatic C-H bond halogenation using lithium halides as halogenating reagents

Synlett

Volumn , Issue 7, 2011, Pages 1038-1042

  Lu, Yongzhong ^a   Wang, Ruiping ^a   Qiao, Xixue ^a   Shen, Zengming ^b  

^a SHANGHAI NORMAL UNIVERSITY   (China)

^b SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

arylpyridines; C H activation; copper; halogenation; lithium halide

Indexed keywords

2 (2,6 DICHLORO 4 METHYLPHENYL)PYRIDINE; AMIDE; AROMATIC COMPOUND; BROMIDE; CARBOXYLIC ACID DERIVATIVE; CERIUM; CHLORIDE; COPPER; HYDROGEN PEROXIDE; ISOXAZOLINE DERIVATIVE; LITHIUM DERIVATIVE; MANGANESE DIOXIDE; PALLADIUM; PERMANGANATE POTASSIUM; PEROXYDISULFATE POTASSIUM; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; SODIUM PEROXIDE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHLORINATION; CROSS COUPLING REACTION; HALOGENATION; HYDROGEN BOND; STOICHIOMETRY;

EID: 79954577237     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259729     Document Type: Article

References (31)

1. For reviews, see:, Dyker G, Angew. Chem. Int. Ed. 1999 38 1698
2. Ritleng V, Sirlin C, Pfeffer M, Chem. Rev. 2002 102 1731; and references cited therein
3. Giri R, Shi B.-F, Engle K M., Maugel N, Yu J.-Q, Chem. Soc. Rev. 2009 38 3242
4. Lyons T W., Sanford M S., Chem. Rev. 2010 110 1147
5. Bellina F, Rossi R, Chem. Rev. 2010 110 1082
6. Colby D A., Bergman R G., Ellman J A., Chem. Rev. 2010 110 624
7. For representative examples of the copper-catalyzed C-C bond formation, see:, Tang B X., Song R J., Wu C Y., Liu Y, Zhou M B., Wei W T., Deng G B., Yin D L., Li J H., J. Am. Chem. Soc. 2010 132 8900
8. Mousseau J J., Bull J A., Charette A B., Angew. Chem. Int. Ed. 2010 49 1115
9. Do H Q., Daugulis O, Org. Lett. 2010 12 2517
10. Kawano T, Matsuyama N, Hirano K, Satoh T, Miura M, J. Org. Chem. 2010 75 1764
11. Yotphan S, Bergman R G., Ellman J A., Org. Lett. 2009 11 1511
12. Li C.-J, Acc. Chem. Res. 2009 42 335
13. For representative examples of the copper-catalyzed C-heteroatom bond formation, see:, Kawano T, Hirano K, Satoh T, Miura M, J. Am. Chem. Soc. 2010 132 6900
14. Zhang L N., Ang G Y., Chiba S, Org. Lett. 2010 12 3682
15. Bernini R, Fabrizi G, Sferrazza A, Cacchi S, Angew. Chem. Int. Ed. 2009 48 8078
16. Wang W H., Luo F, Zhang S H., Cheng J, J. Org. Chem. 2010 75 2415
17. King A E., Huffman L M., Casitas A, Costas M, Ribas X, Stahl S S., J. Am. Chem. Soc. 2010 132 12068
18. Ullmann's Encyclopedia of Industrial Chemistry 6th ed. Wiley-VCH Weinheim 2002
19. Davos S G., Organotransition Metal Chemistry: Application to Organic Synthesis Pergamon Press Oxford 1982
20. Sasson Y, In The Chemistry of Functional Group: The Chemistry of Halides, Pseudo-halides and Azides Part 1, Suppl. D2 Patai S Rappoport Z John Wiley and Sons Chichester 1995
21. de la Mare P D. B., Electrophilic Halogenation Cambridge University Press New York 1976
22. Wan X B., Ma Z X., Li B J., Zhang K Y., Cao S K., Zhang S W., Shi Z J., J. Am. Chem. Soc. 2006 128 7416
23. Kalyani D, Dick A R., Anani W Q., Sanford M S., Org. Lett. 2006 8 2523
24. Song B R., Zheng X J., Mo J, Xu B, Adv. Synth. Catal. 2010 352 329
25. Zheng X J., Song B R., Li G F., Liu B X., Deng H M., Xu B, Tetrahedron Lett. 2010 51 6641
26. Mei T.-S, Giri R, Maugel N, Yu J.-Q, Angew. Chem. Int. Ed. 2008 47 5215
27. Chen X, Hao X S., Goodhue C E., Yu J.-Q, J. Am. Chem. Soc. 2006 128 6790
28. Yang L J., Lu Z, Stahl S S., Chem. Commun. 2009 6460
29. Menini L, Gusevskaya E V., Chem. Commun. 2006 209
30. Menini L, Parreira L A., Gusevskaya E V., Tetrahedron Lett. 2007 48 6401
31. Barnes J C., Hume D N., Inorg. Chem. 1963 2 444