Radical carbonylations with fluorous allyltin reagents

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2367-2370

  Ryu, Ilhyong ^a   Niguma, Tatsuro ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a   Luo, Zhiyong ^b   Curran, Dennis P ^b  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON MONOXIDE; CARBONYL DERIVATIVE; FLUORIDE; KETONE; RADICAL; REAGENT; TIN DERIVATIVE;

ARTICLE; BINDING COMPETITION; CHEMICAL REACTION; EXTRACTION; SYNTHESIS;

EID: 0033583294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00188-4     Document Type: Article

References (24)

1. 1. Recent reviews: (a) Curran, D. P. Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
2. (b) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641-650.
3. (c) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S. -Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826.
4. 2. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532.
5. 3. For the kinetic data of 1, see: Horner, J. H.; Martinez, F. N.; Newcomb, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 2783-2786.
6. 4. Curran, D. P.; Hadida, S.; He, M. J. Org. Chem. 1997, 62, 6714-6715.
7. 5. Kainz, S.; Luo, Z.; Curran, D. P.; Leitner, W. Synthesis 1998, 1425-1427.
8. 6. For a review, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. 1996, 35, 1050-1066. Also see a review on radical C1 synthons:
9. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-206.
10. 7. Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883-7886.
11. 8. For recent examples on the use of allyltin compounds as UMCT (unimolecular chain transfer) radical mediator, see: (a) Enholm, E. J.; Moran, K. M.; Whitley, P. E. Tetrahedron Lett. 1998, 39, 971-974.
12. (b) Tanimoto, H.; Oritani, T. Synlett 1997, 685-686.
13. (c) Clive, D. L. J.; Paul, C. C.; Wang, Z. J. Org. Chem. 1997, 62, 7028-7032 (this paper includes an excellent survey of the original work).
14. (d) Miura, K.; Itoh, D.; Hondo, T.; Saito, H.; Itoh, H.; Hosomi, A. Tetrahedron Lett. 1996, 37, 8539-8542.
15. (e) Fhal, A. -R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661-2664.
16. 9. (a) Ryu, I.; Yamazaki, H.; Kusano, K.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 8558-8560.
17. (b) Ryu, I.; Yamazaki, H.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993, 115, 1187-1189.
18. (c) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615-14626.
19. 10. For the use of 2a in Keck-type radical allylation, see: Curran, D. P.; Luo, Z.; Degenkolb, P. Bioorganic & Med. Chem. Lett. 1998, 8, 2403-2408.
20. 11. Curran, D. P.; Luo, Z. Med. Chem. Res. 1998, 8, 261-265.
21. 2, exhibited poor reactivity for radical allylation reactions, see reference 11.
22. 13. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450-451.
23. 14. A mixture of perfluoroalkanes, purchased from 3M Co. Ltd.
24. 15. Control experiments showed that interconversions among allyltin reagents and iodotin compounds are negligible under these conditions.