Copper-catalyzed halogenation of arylboronic acids

Tetrahedron Letters

Volumn 52, Issue 16, 2011, Pages 1993-1995

  Zhang, Guangyou ^a   Lv, Guanglei ^a   Li, Liping ^a   Chen, Fan ^a   Cheng, Jiang ^a,b  

^a WENZHOU UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; COPPER; FUNCTIONAL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; HALOGENATION;

EID: 79952736769     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.075     Document Type: Article

References (16)

1. (a) Hudlicky, M.; Hudlicky, T. Formation of Carbon-Halogen Bonds In Supplement D: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.: The Chemistry of Functional Groups; Wiley Sons: Chichester, U.K., 1983; pp 1021-1172. Chapter 22;
2. (b) Sasson, Y. Formation of Carbon-Halogen Bonds (Cl, Br, I) In Supplement D: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.: The Chemistry of Functional Groups; Wiley Sons: Chichester, U.K., 1995; pp 535-628. Chapter 11.
3. Urch, C. J. Vinyl and Aryl Halides In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Ley, S. V., Eds.; Elsevier: Oxford, U.K., 1995; 2, pp 605-633.
4. Thiebes, C.; Prakash, G. K. S.; Petasis, N.; Olah, G. A. Synlett 1998, 141.
5. Clough, J. M.; Diorazio, L. J.; Widdowson, D. A. Synlett 1990, 761.
6. Petasis, N. A.; Zavialov, I. A. Tetrahedron Lett. 1996, 37, 567.
7. Wu, H.; Hynes, J., Jr. Org. Lett. 2010, 12, 1192.
8. Kabalka, G. W.; Sastry, K. A. R.; Sastry, U.; Somayaji, V. Org. Prep. Proced. Int. 1982, 14, 359.
9. Szumigala, R. H., Jr.; Devine, P. N.; Gauthier, D. R., Jr.; Volante, R. P. J. Org. Chem. 2004, 69, 566.
10. For selected examples, please see: (a) Zhang, Z. H.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331;
11. (b) Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389;
12. (c) Chu, L. L.; Qing, F.-L. Org. Lett. 2010, 12, 5060;
13. (d) Takaya, J.; Tadami, S.; Ukai, K.; Iwasawa, N. Org. Lett. 2008, 10, 2697;
14. (e) Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2006, 128, 8706.
15. The chlorination of arylboron, see Refs. 6, and 8 and: Murphy, J. M.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 15434.
16. General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol %), 1,10-phen (7.2 mg, 20 mol %) and DMF (2 mL). The mixture was stirred at 80 or 130°C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.