Catalytic Appel reactions

Pure and Applied Chemistry

Volumn 85, Issue 4, 2013, Pages 817-828

  van Kalkeren, Henri A ^a   van Delft, Floris L ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Appel reaction; Bromination; Chlorination; Organocatalysis; Triphenylphosphine

Indexed keywords

APPEL REACTION; BROMINATION; CHLORINATION REACTIONS; CYCLIC PHOSPHINES; ORGANOCATALYSIS; PHOSPHINE OXIDE; PURIFICATION ISSUES; TRIPHENYL PHOSPHINES;

CATALYSIS; CHLORINATION; PHOSPHORUS COMPOUNDS; REACTION KINETICS;

CATALYSTS;

EID: 84875716644     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-12-06-13     Document Type: Article

References (76)

1. K. C. K. Swamy, N. N. B. Kumar, E. Balaraman, K. V. P. P. Kumar. Chem. Rev. 109, 2551 (2009).
2. I. M. Downie, J. B. Holmes, J. B. Lee. Chem. Ind. (London) 900 (1966).
3. B. Castro, C. Selve. Bull. Soc. Chim. Fr. 2296 (1971)
4. R. G. Weiss, E. I. Snyder. J. Org. Chem. 36, 403 (1971)
5. J. Hooz, S. S. H. Gilani. Can. J. Chem. 46, 86 (1968).
6. Work on the mechanism of the three-component system (chlorinations of alcohol): R. Appel, F. Knoll, W. Miche, W. Morbach, H.-D. Wihler, H. Veltmann. Chem. Ber. 109, 58 (1976)
7. R. Appel, K. Warning. Chem. Ber. 108, 606 (1975).
8. Chlorination of (thio)amides and ureas: R. Appel, K. Warning, K. D. Ziehn. Chem. Ber. 107, 698 (1974)
9. R. Appel, K. Ziehn, K. Warning. Chem. Ber. 106, 2093 (1973)
10. R. Appel, K. Warning, K. D. Ziehn. Chem. Ber. 106, 3450 (1973).
11. Induction of Beckmann rearrangement and subsequent chlorination of ketoximes: R. Appel, K. Warning. Chem. Ber. 108, 1437 (1975).
12. Phosphoric and phosphonic ester bond formation: R. Appel, H. Einig. Z. Anorg. Allg. Chem. 414, 236 (1975).
13. Isocyanate synthesis from carbamoyl halides: R. Appel, K. Warning, K. D. Ziehn, A. Gilak. Chem. Ber. 107, 26714 (1974).
14. Nitriles from terminal amides: R. Appel, R. Kleinstu, K. D. Ziehn. Chem. Ber. 104, 1030 (1971).
15. Extensive work on P-N bond constructions: R. Appel, P. Volz. Chem. Ber. 108, 623 (1975)
16. R. Appel, G. Saleh. Chem. Ber. 106, 3455 (1973)
17. R. Appel, G. Saleh. Liebigs Ann. Chem. 766, 98 (1973)
18. R. Appel, R. Kleinstück, K.-D. Ziehn. Chem. Ber. 105, 2476 (1972)
19. R. Appel, R. Kleinstück, K. D. Ziehn, F. Knoll. Chem. Ber. 103, 3631 (1970)
20. R. Appel, R. Kleinstück, K.-D. Ziehn. Chem. Ber. 104, 2250 (1971)
21. R. Appel, B. Blaser, G. Siegemund. Z. Anorg. Allg. Chem. 363, 176 (1968)
22. R. Appel, B. Blaser, R. Kleinstück, K.-D. Ziehn. Chem. Ber. 104, 1847 (1971).
23. R. Appel. Angew. Chem., Int. Ed. 14, 801 (1975).
24. R. Appel, M. Halstenberg. In Organophosphorus Reagents in Organic Synthesis, J. I. G. Cardogan (Ed.), pp. 387-424, Academic Press, London (1979).
25. J. Baraniak, W. J. Stec. Tetrahedron Lett. 26, 4379 (1985)
26. C. Lensink, B. de Ruiter, J. C. van de Grampel. J. Chem. Soc., Dalton Trans. 1521 (1984)
27. I. Pinter, J. Kovacs, A. Messmer. Carbohydr. Res. 53, 117 (1977).
28. D. G. Gilheany. Chem. Rev. 94, 1339 (1994).
29. Y. Nishida, Y. Shingu, H. Dohi, K. Kobayashi. Org. Lett. 5, 2377 (2003).
30. K. V. Rajendran, J. S. Kudavalli, K. S. Dunne, D. G. Gilheany. Eur. J. Org. Chem. 2720 (2012)
31. J. J. Li. In Name Reactions, pp. 10-11, Springer, Berlin (2006)
32. K. A. Roper, H. Lange, A. Polyzos, M. B. Berry, I. R. Baxendale, S. V. Ley. Beilstein J. Org. Chem. 7, 1648 (2011).
33. Several web sources now also define the Appel reaction specifically as the halogenation of alcohols: http://www.organic-chemistry.org/namedreactions/appel-reaction.shtm; http://en.wikipedia.org/wiki/Appel_reaction/; http://www.namereactions.org/name-reactions/ appel-reaction/; http://www.synarchive.com/named-reactions/Appel_Reaction/; http://www.organic-reaction.com/organic-synthesis/functional-group-synthesis/halides-derivatives/
34. B. A. Arbusow. Pure Appl. Chem. 9, 307 (1964).
35. G. Wittig. Nobel Lecture, 1979.
36. O. I. Kolodiazhnyi. Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim (1999)
37. H. Pommer. Angew. Chem., Int. Ed. 16, 423 (1977).
38. R. Engel. Handbook of Organophosphorus Chemistry, Marcel Dekker, New York (1992)
39. S. Kobayashi, M. Suzuki, T. Saegusa. Polym. Bull. (Berlin) 8, 417 (1982).
40. M. Guinó, K. K. M. Hii. Chem. Soc. Rev. 36, 608 (2007)
41. E. Arstad, A. G. M. Barrett, B. T. Hopkins, J. Kobberling. Org. Lett. 4, 1975 (2002)
42. S. Dandapani, D. P. Curran. Chem.-Eur. J. 10, 3130 (2004).
43. C. W. Lindsley, Z. Zhao, R. C. Newton, W. H. Leister, K. A. Strauss. Tetrahedron Lett. 43, 4467 (2002)
44. S. Dandapani, D. P. Curran. Tetrahedron 58, 3855 (2002)
45. J. C. Bottaro. Synth. Commun. 15, 195 (1985).
46. P. A. Byrne, K. V. Rajendran, J. Muldoon, D. G. Gilheany. Org. Biomol. Chem. 10, 353137 (2012).
47. C. J. Li, B. M. Trost. Proc. Natl. Acad. Sci. USA 105, 13197 (2008)
48. B. M. Trost. Science 254, 1471 (1991)
49. D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey, J. L. Leazer Jr., R. J. Linderman, K. Lorenz, J. Manley, B. A. Pearlman, A. Wells, A. Zaks, T. Y. Zhang. Green Chem. 9, 411 (2007).
50. D. Cordell, J. O. Drangert, S. White. Global Environ. Change 19, 292 (2009)
51. EcoSanRes Stockholm Environment Institute (SEI) funded by SIDA Stockholm, Closing the Loop on Phosphorus (2003), http://www.ecosanres.org/pdf_files/ESR-factsheet-04.pdf
52. V. Smil. Annu. Rev. Energ. Environ. 25, 53 (2000).
53. S. P. Marsden. Nat. Chem. 1, 685 (2009)
54. I. J. S. Fairlamb. ChemSusChem 2, 1021 (2009).
55. S. P. Marsden, A. E. McGonagle, B. McKeever-Abbas. Org. Lett. 10, 2589 (2008)
56. T. W. Campbell, J. J. Monagle. Org. Synth. 43, 31 (1963)
57. T. W. Campbell, J. J. Monagle, V. S. Foldi. J. Am. Chem. Soc. 84, 3673 (1962)
58. T. W. Campbell, J. J. Monagle. J. Am. Chem. Soc. 84, 1493 (1962).
59. R. M. Denton, J. An, B. Adeniran, A. J. Blake, W. Lewis, A. M. Poulton. J. Org. Chem. 76, 6749 (2011)
60. R. M. Denton, J. An, B. Adeniran. Chem. Commun. 3025 (2010).
61. R. M. Denton, J. An, P. Lindovska, W. Lewis. Tetrahedron 68, 2899 (2012)
62. R. M. Denton, X. Tang, A. Przeslak. Org. Lett. 4678 (2010).
63. C. J. O'Brien, J. L. Tellez, Z. S. Nixon, L. J. Kang, A. L. Carter, S. R. Kunkel, K. C. Przeworski, G. A. Chass. Angew. Chem., Int. Ed. 48, 6836 (2009).
64. J. R. Harris, M. T. Haynes, A. M. Thomas, K. A. Woerpel. J. Org. Chem. 75, 5083 (2010).
65. H. A. van Kalkeren, J. J. Bruins, F. P. J. T. Rutjes, F. L. van Delft. Adv. Synth. Catal. 354, 1417 (2012)
66. H. A. van Kalkeren, S. H. A. M. Leenders, C. A. Hommersom, F. P. J. T. Rutjes, F. L. van Delft. Chem.-Eur. J. 17, 11290 (2011).
67. L. D. Quin. A Guide to Organophosphorus Chemistry, John Wiley, New York (2000)
68. L. D. Quin, G. Keglevich, A. S. Ionkin, R. Kalgutkar, G. Szalontai. J. Org. Chem. 61, 7801 (1996).
69. N. Campbell, A. H. Scott. J. Chem. Soc. C 1050 (1966)
70. G. Wittig, A. Maercker. Chem. Ber. 97, 747 (1964).
71. H. Firouzabadi, N. Iranpoor, F. Ebrahimzadeh. Tetrahedron Lett. 47, 1771 (2006).
72. G. A. Wiley, R. L. Hershkowitz, B. M. Rein, B. C. Chung. J. Am. Chem. Soc. 86, 964 (1964).
73. S. Hanessian, M. M. Ponpipom, P. Lavallee. Carbohydr. Res. 24, 45 (1972).
74. E. D. Matveeva, T. A. Podrugina, N. S. Zefirov. Mendeleev Commun. 8, 21 (1998).
75. A. K. Bose, B. Lal. Tetrahedron Lett. 3937 (1973).
76. Q. Sun, S. Cai, B. R. Peterson. Org. Lett. 11, 567 (2008).