Radical cyanocarbonylation using alkyl allyl sulfone precursors

Synlett

Volumn , Issue 20, 2005, Pages 3160-3162

  Kim, Sangmo ^a   Cho, Chang Ho ^a   Kim, Sunggak ^a   Uenoyama, Yoshitaka ^b   Ryu, Ilhyong ^b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Osaka Prefecture University   (Japan)

Author keywords

Acyl radical; Alkyl allyl sulfone; Carbon monoxide; Cyanocarbonylation; Tin free radical reaction

Indexed keywords

4 TOLYLSULFONYL CYANIDE; CARBON MONOXIDE; CYANIDE; SULFONE DERIVATIVE; TIN; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 29744434769     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921932     Document Type: Article

References (38)

1. For a review on acyl cyanides, see: (a) Thesing, J.; Witzel, D.; Brehm, A. Angew. Chem. 1956, 68, 425.
2. (b) Hünig, S.; Schaller, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 36.
3. For recent reports on acyl cyanides see: (a) Yamamoto, Y.; Kinpara, K.; Saigoku, T.; Takagishi, H.; Okuda, S.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 605.
4. (b) Duplais, C.; Bures, F.; Sapountzis, I.; Tobias, T. J.; Cahiez, G.; Knochel, P. Angew. Chem. Int. Ed. 2004, 43, 2968.
5. (c) Watahiki, T.; Ohba, S.; Oriyama, T. Org. Lett. 2003, 5, 2679.
6. (d) Yoo, B. W.; Kim, D. Y.; Choi, J. W.; Hwang, S. K.; Choi, K. I.; Kim, J. H. Bull. Korean Chem. Soc. 2003, 24, 263.
7. (e) Saikia, P.; Laskar, D. D.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 2002, 43, 7525.
8. (f) Yoo, B. W.; Hwang, S. K.; Kim, D. Y.; Choi, J. W.; Ko, J. J.; Choi, K. I.; Kim, J. H. Tetrahedron Lett. 2002, 43, 4813.
9. (a) Cao, Y.-Q.; Du, Y.-F.; Chen, B.-H.; Li, J.-T. Synth. Commun. 2004, 34, 2951.
10. (b) Olah, G. A.; Arvanaghi, M.; Prakash, G. K. S. Synthesis 1983, 636.
11. (c) Ando, T.; Kawate, T.; Tamawaki, J.; Hanafusa, T. Synthesis 1983, 637.
12. Tanaka, M. Bull. Chem. Soc. Jpn. 1981, 54, 637.
13. (a) Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209.
14. (b) Guyader, F. L.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. J. Am. Chem. Soc. 1997, 119, 7410.
15. (c) Xiang, J.; Jiang, W.; Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1997, 119, 4123.
16. (d) Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 1998, 37, 2864.
17. (e) Bertrand, F.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem. Int. Ed. 1999, 38, 1943.
18. (a) Kim, S.; Lim, C. J. Angew. Chem. Int. Ed. 2002, 41, 3265.
19. (b) Kim, S.; Song, H.-J. Synlett 2002, 2110.
20. (c) Kim, S.; Lim, C. J. Bull. Korean Chem. Soc. 2003, 24, 1219.
21. (d) Lee, S.; Lim, C. J.; Kim, S. Bull. Korean Chem. Soc. 2004, 25, 1611.
22. Kim, S.; Kim, S.; Otsuka, N.; Ryu, I. Angew. Chem. Int. Ed. 2005, 44, 6183.
23. For examples of radical reactions involving two radical C1 synthons, see: (a) Ryu, I.; Kuriyama, H.; Minakata, S.; Komatsu, M.; Yoon, J.-Y.; Kim, S. J. Am. Chem. Soc. 1999, 121, 12190.
24. (b) Ryu, I.; Kuriyama, H.; Miyazato, H.; Minakata, S.; Komatsu, M.; Yoon, J.-Y.; Kim, S. Bull. Chem. Soc. Jpn. 2004, 77, 1407.
25. For reviews on acyl radicals and radical carbonylations, see: (a) Chatgilialogu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
26. (b) Ryu, I.; Sonoda, N. Angew. Chem. Int. Ed. 1996, 35, 1050.
27. (c) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
28. -1.
29. (a) Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1980, 21, 731.
30. (b) Bal, B. S.; Childers, W. E. Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
31. Similarly, quenching with aniline afforded the corresponding amide in 78% yield.
32. Smith, T. A. K.; Whitham, G. H. J. Chem. Soc., Chem. Commun. 1985, 897.
33. For a primary acyl radical, see: (a) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1995, 60, 7384.
34. (b) For a secondary acyl radical, see: Boese, W. T.; Goldman, A. S. Tetrahedron Lett. 1992, 33, 2119.
35. (c) For decarbonylation rates of acyl radicals, see: Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Pedrielli, P. Organometallics 1995, 14, 2672.
36. (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670.
37. (b) Ryu, I.; Kreimerman, S.; Araki, F.; Nishitani, S.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 2002, 124, 3812.
38. +] = 208.1099; found: 208.1096.