Synthetic radical reactions using dibutylchlorogermane and dibutylethoxygermane as radical mediators

Synlett

Volumn , Issue 20, 2005, Pages 3151-3153

  Miura, Katsukiyo ^a   Ootsuka, Kazunori ^a   Hosomi, Akira ^a,b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b National Institution for Academic Degrees and University Evaluation Tokyo   (Japan)

Author keywords

Addition reactions; Halides; Organometallic reagents; Radical reactions; Reductions

Indexed keywords

ALKANE; ALKENE; BROMIDE; DIBUTYLCHLOROGERMANE; DIBUTYLETHOXYGERMANE; GERMANIUM DERIVATIVE; HALIDE; HALOGEN; IODIDE; ORGANOMETALLIC COMPOUND; RADICAL; REAGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 29744457086     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921927     Document Type: Article

References (27)

1. (a) Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, 2001.
2. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
3. (c) Curran, D. P. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Chap. 4.1 and 4.2, 715.
4. (d) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
5. Boyer, I. J. Toxicology 1989, 55, 253.
6. Baguley, P. A.; Walton, J. C. Angew. Chem. Int. Ed. 1998, 37, 3073; and references therein.
7. (a) Giese, B.; Kopping, B.; Chatgilialoglu, C. Tetrahedron Lett. 1989, 30, 681.
8. (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
9. (c) Chatgilialoglu, C.; Guerra, M.; Guerrini, A.; Seconi, G. J. Org. Chem. 1992, 57, 2427.
10. (d) Yamazaki, O.; Togo, H.; Matsubayashi, S.; Yokoyama, M. Tetrahedron 1999, 55, 3735.
11. (e) Studer, A.; Amrein, S.; Schleth, F.; Schulte, T.; Walton, J. C. J. Am. Chem. Soc. 2003, 125, 5726.
12. (a) Sakurai, H.; Mochida, K.; Hosomi, A.; Mita, F. J. Organomet. Chem. 1972, 38, 275.
13. (b) Chatgilialoglu, C.; Ballestri, M. Organometallics 1995, 14, 5017.
14. (c) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2001, 74, 747.
15. For the hydrogermane-mediated intermolecular radical addition of iodoalkanes, see: (a) Pike, P.; Hershberger, S.; Hershberger, J. Tetrahedron Lett. 1985, 26, 6289.
16. (b) Pike, P.; Hershberger, S.; Hershberger, J. Tetrahedron 1988, 44, 6295.
17. (a) Inoue, K.; Sawada, A.; Shibata, I.; Baba, A. J. Am. Chem. Soc. 2002, 124, 906.
18. (b) Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2005, 7, 3093.
19. (c) Takami, K.; Mikami, S.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Tetrahedron 2003, 59, 6627; and references therein.
20. Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. J. Org. Chem. 1993, 58, 6838; and references therein.
21. 2. For the last step, see: Ohshita, J.; Toyoshima, Y.; Iwata, A.; Tang, H.; Kunai, A. Chem. Lett. 2001, 886.
22. (b) For the preparation of 1a, see also: Satge, J. Ann. Chim. 1961, 6, 519.
23. 2 (1.2 equiv) for 24 h gave 3a in 34% yield with recovery of 2a (ca. 50%).
24. (a) Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674.
25. (b) Gualtieri, G.; Geib, S. J.; Curran, D. P. J. Org. Chem. 2003, 68, 5013.
26. Newcomb, M. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001, Chap. 3.1, 317.
27. -1. See: Chatgilialoglu, C.; Ballestri, M.; Escudié, J.; Pailhous, I. Organometallics 1999, 18, 2395.