SmI2-mediated sequential radical cyclization/anionic capture of aryl iodides on solid support

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2281-2284

  Du, Xiaohui ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IODINE DERIVATIVE; SAMARIUM;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032537215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00292-5     Document Type: Article

References (19)

1. 1. For reviews, see: (a) Chem. Rev. 1997, 97, whole issue of No. 2, pp 347-510.
2. (b) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337.
3. (c) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
4. 2. Chen, S.; Janda, K. D. J. Am. Chem. Soc. 1997, 119, 8724-8725.
5. 3. (a) Fruchtel, J. S. and Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42.
6. (b) Hermkens, P. H.H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 52, 4527-4554.
7. (c) Armstrong, R. W.; Combs A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res., 1996, 29, 123-131.
8. 2-mediated reactions, see: Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338.
9. 2-mediated sequential radical cyclization/anionic capture of aryl iodides, see: (a) Curran, D. P.; Fevig, T. L.; Totleben, M. J. Synlett, 1990, 773-774.
10. (b) Molander, G. A.; Harring, L. S. J. Org. Chem. 1990, 55, 6171-6176.
11. (c) Curran, D. P.; Totleben, M; J. J. Am. Chem. Soc. 1992, 114, 6050-6058.
12. 6. Du, X.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5678-5679.
13. 3, DMF.
14. 8. Under the same condition, reaction of crotyloxy-2-iodo benzene had 79% deuterium incorporation and no radical disproportionation. This agreed well with the literature (reference 5).
15. 2 instead of being captured.
16. 10. Wright, P.; Lloyd, D.; Rapp, W.; Andrus, A. Tetrahedron Lett. 1993, 34, 3373-3376.
17. 2.
18. 13C NMR).
19. 13. The capture of branched aldehydes such as 2,2-dimethyl propionaldehyde on resin was only slightly better than that of butyraldehyde.