Reductive dehalogenation of aryl bromides and chlorides and their use as aryl blocking groups

Synthesis

Volumn , Issue 2, 2010, Pages 217-220

  Ramanathan, Ahalya ^a   Jimenez, Leslie S ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Arenes; Halides; Hydrogenation; Reductions; Regioselectivity

Indexed keywords

ARENES; AROMATIC RINGS; ARYL BROMIDES; CARBOXYLIC ACID GROUPS; CATALYTIC HYDROGENATION; FUNCTIONALIZED; HALIDES; NEUTRAL CONDITIONS; ORTHO POSITION; REDUCTIVE DEHALOGENATION;

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CARBOXYLIC ACIDS; CHLORINE COMPOUNDS; DEHALOGENATION; ORGANIC ACIDS; REGIOSELECTIVITY;

HYDROGENATION;

AROMATIC COMPOUND; BROMIDE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; CHLORINE DERIVATIVE; KETONE DERIVATIVE; NITRILE; NITRO DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; DEHALOGENATION; HYDROGENATION; REDUCTION; SYNTHESIS;

EID: 73949114833     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217112     Document Type: Article

References (39)

1. Sen A B., Kulkarni Y D., J. Indian Chem. Soc. 1956 33 326, Sakellarios E, Jatrides D, Ber. Dtsch. Chem. Ges. 1925 58 2286
2. Tashiro M, Yamato T, J. Org. Chem. 1979 44 3037, Tashiro M, Yamato T, Kobayashi K, J. Org. Chem. 1984 49 4724, Olah G A., Prakash G K. S., Iyer P S., Tashiro M, Yamato T, J. Org. Chem. 1987 52 1881
3. For 2-alkenylanilines, see:, Moutrille C, Zard S Z., Tetrahedron Lett. 2004 45 4631 For anilines substituted with sulfur nucleophiles at the 2-position, see:, Zhu L, Zhang M, J. Org. Chem. 2004 69 7371 For ortho hydroxybenzylation and hydroxyalkylation of secondary anilines, see:, Sugasawa T, Toyoda T, Adachi M, Sasakura K, J. Am. Chem. Soc. 1978 100 4842 For ortho substitution of arylsydnones, see:, Lin S T., Cheo H S., Chen B I., Own Z Y., Heteroat. Chem. 1998 9 549 For ortho substitution of phenols with vinyl ethers, see:, Copeland C M., Ghosh J, McAdam D P., Skelton B W., Stick R V., White A H., Aust. J. Chem. 1988 41 69
4. Pinder A R., Synthesis 1980 425
5. Choi H Y., Chi D Y., J. Am. Chem. Soc. 2001 123 9202, Adimurthy S, Ramachandraiah G, Bedekar A V., Tetrahedron Lett. 2003 44 6391, Adimurthy S, Ramachandraiah G, Tetrahedron Lett. 2004 45 5251
6. Tashiro M, Watanabe H, Tsuge O, Org. Prep. Proced. Int. 1975 7 43
7. Effenberger F, Angew. Chem. Int. Ed. 2002 41 1699
8. van Zijl P C. M., Jenneskens L W., Bastiaan E W., MacLean C, de Wolff W H., Bickelhaupt F, J. Am. Chem. Soc. 1986 108 1415, Jensen J, Tejler J, Waernmark K, J. Org. Chem. 2002 67 6008, Pyne S G., Boche G, J. Org. Chem. 1989 54 2663
9. Cortese N A., Heck R F., J. Org. Chem. 1977 42 3491, Wiener H, Blum J, Sasson Y, J. Org. Chem. 1991 56 6145
10. Tashiro M, Fukata G, J. Org. Chem. 1977 42 835
11. Pri-Bar I, Buchman O, J. Org. Chem. 1986 51 734
12. Shankar R B., Pews R G., J. Heterocycl. Chem. 1993 30 169, Takahashi M, Konishi H, Iida S, Nakamura K, Yamamura S, Nishiyama S, Tetrahedron 1999 55 5295
13. Manet I, Monti S, Fagnoni M, Protti S, Albini A, Chem. Eur. J. 2005 11 140
14. Pews R G., Hunter J E., Wehmeyer J M., Tetrahedron 1993 49 4809
15. Boyer S K., Bach J, McKenna J, Jagdmann E Jr., J. Org. Chem. 1985 50 3408
16. Lassova L, Lee H K., Hor T S. A., J. Mol. Catal. A: Chem. 1999 144 397
17. Zhang Y, Liao S, Xu Y, Tetrahedron Lett. 1994 35 4599
18. Marques C A., Selva M, Tundo P, J. Org. Chem. 1993 58 5256
19. Monguchi Y, Kume A, Hattori K, Maegawa T, Saiiki H, Tetrahedron 2006 62 7926
20. Weissermel K, Arpe H.-J, Industrial Organic Chemistry 2nd ed. VCH Weinheim 1993 23, Mukhopadhyay S, Rothenberg G, Wiener H, Sasson Y, Tetrahedron 1999 55 14763
21. Visser G W. M., Halteren B W. v, Herscheid J D. M., Brinkman G A., Hoekstra A, J. Chem. Soc., Chem. Commun. 1984 655
22. Banks R E., Mohialdin-Khaffaf S N., Lal G S., Sharif I, Syvret R G., J. Chem. Soc., Chem. Commun. 1992 595
23. Zhang Y, Feng J, Li C.-J, J. Am. Chem. Soc. 2008 130 2900
24. Einhorn J, Luche J L., J. Org. Chem. 1987 52 4124
25. Ghiaci M, Kalbasi R J., Mollahasani M, Aghaei H, Appl. Catal. A 2007 320 35
26. Naeimi H, Moradi L, J. Mol. Catal. A: Chem. 2006 256 242
27. Wan X, Ma Z, Li B, Zhang K, Cao S, Zhang S, Shi Z, J. Am. Chem. Soc. 2006 128 7416
28. McNulty R, Nair J J., Robertson J, Org. Lett. 2007 9 4575
29. Bertorello H E., Rossi R A., Rossi R H., J. Org. Chem. 1970 35 3332
30. Kolehmainen E, Laihia K, Kauppinen R, Rasala D, Puchala A, J. Phys. Org. Chem. 1995 8 577
31. Ungnade H E., J. Am. Chem. Soc. 1954 76 5133
32. Augustine R L., Gustavsen A J., Wanat S F., Pattison I C., Houghton K S., Koletar G, J. Org. Chem. 1973 38 3004
33. Chazin W J., Colebrook L D., Magn. Reson. Chem. 1985 23 597
34. Yoshida T, Mori K, He G, Heterocycles 1995 41 1923, Miura K, Inagaki T, Nakatani N, Chem. Pharm. Bull. 1989 37 1816
35. Erman W F., Treptow R S., Bakuzis P, Wenkert E, J.Am. Chem. Soc. 1971 93 657
36. Abildgaard J, Bolvig S, Hansen P E., J. Am. Chem. Soc. 1998 120 9063
37. Wawer I, Krysiak T, Kecki Z, J. Mol. Struct. 1994 326 163
38. Sutherland R G., Zhang C.-H, Piorko A, Lee C C., Can. J. Chem. 1989 67 137
39. Sainz-Diaz C I., Hernandez-Laguna A, J. Chem. Soc., Perkin Trans. 2 1999 1489, Ohwada T, Kasuga M, Shudo K, J. Org. Chem. 1990 55 2717