Effective synthesis of benzyl halides triggered by in situ prepared hypervalent halides

Chinese Chemical Letters

Volumn 24, Issue 1, 2013, Pages 45-48

  Ling, Xue Ge ^a   Xiong, Yan ^a   Zhang, Shu Ting ^a   Huang, Ruo Feng ^a   Zhang, Xiao Hui ^a  

^a CHONGQING UNIVERSITY   (China)

Author keywords

Benzyl halides; Bromination; Hypervalent; Iodination

Indexed keywords

EID: 84873740749     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2012.12.013     Document Type: Article

References (30)

1. Y. Sasson Formation of CCl, CBr and CI bonds S. Patai, Z. Rappoport, The Chemistry of Functional Groups, Supplement D2. Part 2. The Chemistry of Halides, Pseudohalides and Azides 1995 John Wiley & Sons Chichester 535 628
2. +: expedient protocol for iodohydroxylation of olefins and iodination of aromatics J. Org. Chem. 74 2009 6287 6290
3. R. Badri, and M. Gorjizadeh A mild, efficient and selective iodination of aromatic compounds using iodine and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate Chin. Chem. Lett. 20 2009 1439 1443
4. 2 system E-J. Chem. 6 2009 1164 1166
5. O.G. Barton, and J. Mattay Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: an efficient way to iodinate alkylated calix[4]arenes Synthesis 2008 110 114
6. 3-catalyzed arene iodination Org. Lett. 12 2010 2104 2107
7. D.D. Tanner, and G.C. Gidley Free-radical iodination. A novel synthetic method J. Am. Chem. Soc. 90 1968 808 809
8. 2 Angew. Chem. Int. Ed. 41 2002 2556 2558
9. R. Montoro, and T. Wirth Direct iodination of alkanes Org. Lett. 5 2003 4729 4731
10. R. Montoro, and T. Wirth Direct bromination and iodination of non-activated alkanes by hypohalite reagents Synthesis 2005 1473 1478
11. J. Barluenga, E. Campos-Gómez, D. Rodriguez, F. González-Bobes, and J.M. González New iodination reactions of saturated hydrocarbons Angew. Chem. Int. Ed. 44 2005 5851 5854
12. 3 as a new reagent system for C-H functionalization in hydrocarbons Tetrahedron Lett. 49 2008 6401 6403
13. H. Shaw, H.D. Perlmutter, C. Gu, S.D. Arco, and T.O. Quibuyen Free-radical bromination of selected organic compounds in water J. Org. Chem. 62 1997 236 237
14. 2 Tetrahedron Lett. 46 2005 487 489
15. A. Podgoršek, S. Stavber, M. Zupan, and J. Iskra Association of fluorous "Phase-Vanishing" method with visible-light activation in benzylic bromination by bromine Eur. J. Org. Chem. 2006 483 488
16. 3reagent J. Org. Chem. 63 1998 6023 6026
17. 2-HBr system Chin. Chem. Lett. 22 2011 382 384
18. R. Mestres, and J. Palenzuela High atomic yield bromine-less benzylic bromination Green Chem. 4 2002 314 316
19. Y. Zhang, K. Shibatomi, and H. Yamamoto Lewis acid catalyzed highly selective halogenation of aromatic compounds Synlett 2005 2837 2842
20. 4 as general, mild and efficient systems for the α-monohalogenation of carbonyl compounds and for benzylic halogenation Tetrahedron Lett. 52 2011 4026 4029
21. M. Akhtar, and D.H.R. Barton Reactions at position 19 in the steroid nucleus. A convenient synthesis of 19-norsteroids J. Am. Chem. Soc. 86 1964 1528 1536
22. D.D. Tanner, G.C. Gidley, N. Das, J.E. Rowe, and A. Potter On the structure of tert-butyl hypoiodite J. Am. Chem. Soc. 106 1984 5261 5267
23. C. Walling, and A. Padwa Positive halogen compounds. V. t-butyl hypobromite and two new techniques for hydrocarbon bromination J. Org. Chem. 27 1962 2976 2977
24. N2 reactions of lithium halide and methyl halide: A microhydration model J. Mol. Model. 16 2010 1931 1937
25. + (X = F, Cl, Br, and I) Int. J. Quantum Chem. 112 2012 2475 2481
26. R. Giri, and J.F. Hartwig Cu(I)-amido complexes in the ullmann reaction: reactions of Cu(I)-amido complexes with iodoarenes with and without autocatalysis by CuI J. Am. Chem. Soc. 132 2010 15860 15863
27. S. Santoro, R.Z. Liao, and F. Himo Theoretical study of mechanism and selectivity of copper-catalyzed C-H bond amidation of indoles J. Org. Chem. 76 2011 9246 9252
28. R.T. Gephart III, C.L. McMullin, and N.G. Sapiezynski Reaction of Cu(I) with dialkyl peroxides: Cu(II)-alkoxides, alkoxy radicals, and catalytic C-H etherification J. Am. Chem. Soc. 134 2012 17350 17353
29. 1H NMR evidence Chin. J. Chem. 29 2011 1143 1148
30. X. Zhang, Y. Xiong, and S.T. Zhang Aldol condensations of aldehydes and ketones catalyzed by primary amine on water Asian J. Chem. 24 2012 751 755