Synthesis of cyclopropane-containing phosphorus compounds by radical coupling of butenylindium with iodo phosphorus compounds

European Journal of Organic Chemistry

Volumn , Issue 11, 2011, Pages 2163-2171

  Kiyokawa, Kensuke ^a   Suzuki, Itaru ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

C C coupling; Cyclopropylmethylation; Indium; Phosphorus; Radical reactions; Tin

Indexed keywords

EID: 79953235405     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001471     Document Type: Article

References (51)

1. K. Moonen, I. Laureyn, C. V. Stevens, Chem. Rev. 2004, 104, 6177-6215.
2. K. Schug, W. Lindner, Chem. Rev. 2005, 105, 67-113.
3. F. Palacios, C. Alonso, J. M. de los Santos, Chem. Rev. 2005, 105, 899-931.
4. L. Horner, H. Hoffmann, H. C. Wipel, G. Klahre, Chem. Ber. 1959, 92, 2499-2505.
5. W. S. Wadsworth, W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733-1738.
6. For a review, see:, J. Boutagy, R. Thomas, Chem. Rev. 1974, 74, 87-99.
7. T. Białas, A. Szadowiak, P. Bałczewski, Heteroat. Chem. 2004, 15, 127-130.
8. P. Bałczewski, M. Mikołajczyk, Synthesis 1995, 392-396.
9. P. Bałczewski, W. M. Pietrzykowski, Tetrahedron 1997, 53, 7291-7304.
10. P. Bałczewski, T. Białas, M. Mikołajczyk, Tetrahedron Lett. 2000, 41, 3687-3690.
11. R. S. Brown, D. F. Eaton, A. Hosomi, T. G. Traylor, J. M. Wright, J. Organomet. Chem. 1974, 66, 249-254.
12. J. San Filippo Jr., J. Silbermann, J. Am. Chem. Soc. 1982, 104, 2831-2836.
13. M. S. Alnajjar, G. F. Smith, H. G. Kuivila, J. Org. Chem. 1984, 49, 1271-1276.
14. A. J. Lucke, D. J. Young, Tetrahedron Lett. 1991, 32, 807-810.
15. A. J. Lucke, D. J. Young, J. Org. Chem. 2005, 70, 3579-3583.
16. M. Yasuda, K. Kiyokawa, K. Osaki, A. Baba, Organometallics 2009, 28, 132-139.
17. For the synthesis of cyclopropylphosphonates, see:, A. A. Azin Quntar, M. Srebnik, J. Org. Chem. 2006, 71, 730-733, and references therein.
18. Recently, reactions introducing a cyclopropyl group by Pd-catalyzed coupling have been extensively studied, see:, C. Shu, K. Sidhu, L. Zhang, X.-j. Wang, D. Krishnamurthy, C. H. Senanayake, J. Org. Chem. 2010, 75, 6677-6680, and references therein.
19. For selected papers, see
20. J. R. Reid, R. S. Marmor, J. Org. Chem. 1978, 43, 999-1001.
21. M. S. Dappen, J. R. Pellicciari, B. Natalini, J. B. Monahan, C. Chiorri, A. A. Cordis, J. Med. Chem. 1991, 34, 161-168.
22. D. Hockova, A. Holy, M. Masojidkova, G. Andrei, R. T. Snoeck, E. De Clercq, J. Med. Chem. 2003, 46, 5064-5073.
23. J.-R. Choi, D.-G. Cho, K. Y. Roh, J.-T. Hwang, S. Ahn, H. S. Jang, W.-Y. Cho, K. W. Kim, Y.-G. Cho, J. Kim, Y. Z. Kim, J. Med. Chem. 2004, 47, 2864-2869.
24. Trace amounts of the ring-opening product, which was not precisely identified, was observed.
25. The reaction using tributyl[(1-methylcyclopropyl)methyl]stannane instead of 1 gave a mixture of cyclopropane-containing product (33 %) and ring-opening product (14 %). See the Supporting Information for details.
26. K. Kiyokawa, M. Yasuda, A. Baba, Org. Lett. 2010, 12, 1520-1523.
27. S. Usugi, T. Tsuritani, H. Yorimitsu, H. Shinokubo, K. Oshima, Bull. Chem. Soc. Jpn. 2002, 75, 841-845.
28. 2 and phosphane oxide species is plausible. For an example of complex formation, see:, B. E. Kucera, M. M. Olmstead, R. S. Tanke, S. M. Kauzlarich, Acta Crystallogr., Sect. E 2003, 59, 359-360.
29. The corresponding reductive products were also obtained as by-products.
30. P. Bałczewski, W. M. Pietrzykowski, Tetrahedron 1996, 52, 13681-13694.
31. When the reaction was carried out in the absence of AIBN, the yield of product 6 decreased to 27 %.
32. [8]
33. X. Creary, B. Benage, M. E. Mehrsheikh-Mohammadi, J. P. Bays, Tetrahedron Lett. 1985, 26, 2383-2386.
34. Reactions of the α-phosphonyl radical generated by the addition of alkyl radicals to vinylphosphonates were reported, see
35. J. A. Baban, B. P. Roberts, J. Chem. Soc., Chem. Commun. 1979, 373-374.
36. J. A. Baban, B. P. Roberts, J. Chem. Soc. Perkin Trans. 2 1981, 161-166.
37. J. A. Baban, B. P. Roberts, J. Chem. Soc. Perkin Trans. 2 1988, 1195-1200.
38. 3 (0.4 mmol) resulted in a lower yield (44 %).
39. [8]
40. E. J. Corey, G. T. Kwiatkowski, J. Am. Chem. Soc. 1966, 88, 5654-5656.
41. M. P. Healy, A. F. Parsons, J. G. T. Rawlinson, Org. Lett. 2005, 7, 1597-1600.
42. B. Iorga, F. Eymery, P. Savignac, Synthesis 2000, 576-580.
43. S. Pignard, C. Lopin, G. Gouhier, S. R. Piettre, J. Org. Chem. 2006, 71, 31-37.
44. I. Pergament, M. Srebnik, Org. Lett. 2001, 3, 217-219.
45. F. Hammerschmidt, H. Kählig, N. Müller, J. Chem. Soc. Perkin Trans. 1 1991, 365-369.
46. A. F. Kluge, Org. Synth. 1986, 64, 80.
47. M.-P. Teulade, P. Savignac, Tetrahedron Lett. 1989, 30, 6327-6330.
48. C. Patois, L. Ricard, P. Savignac, J. Chem. Soc. Perkin Trans. 1 1990, 1577-1581.
49. H. Koto, T. Iwamoto, Synthesis 1985, 982-983.
50. E. M. Schuster, M. Botoshansky, M. Gandelman, Angew. Chem. Int. Ed. 2008, 47, 4555-4558.
51. C. C. Silveira, R. C. Guadagnin, F. Rinaldi, Eur. J. Org. Chem. 2007, 29, 4935-4939.