Triethylborane-induced radical addition of halogenated compounds to alkenes and alkynes in water

Synlett

Volumn , Issue 12, 1998, Pages 1351-1352

  Nakamura, T ^a   Yorimitsu, H ^a   Shinokubo, H ^a   Oshima, K ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 0000891779     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1985     Document Type: Article

References (13)

1. (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH Verlagsgesellschaft mbH.; Weinheim, 1996;
2. (b) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856;
3. (c) Curran, D. P. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H. Eds; Pergamon Press: Oxford, 1991. Vol. 4, Chap. 4.1 p 715;
4. (d) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177-194.
5. Minisci, F. Synthesis 1973, 1-24;
6. Yamazaki, O.; Togo, H.; Nogami, G; Yokoyama, M. Bull. Chem. Soc. Jpn. 1997, 70, 2519-2523.
7. Yorimitsu, H.; Nakamura, T.; Shinokubo, H. Oshima, K. J. Org. Chem. in press.
8. 2: C, 45.88; H, 3.53%.
9. 3B in water.
10. Curran, D. P.; Chang, C. -T. Tetrahedron. Lett. 1987, 28, 2477-2480.
11. 3: C, 31.13; H, 4.11%.
12. 2O (5 mL)), 5 was obtained in 85% yield after stirring for 7 h.
13. Representative experimental procedure: Triethylborane (1.0 M methanol solution, 0.1 mL, 0.1 mmol) was added to a heterogeneous solution of 1b (198 mg, 1.0 mmol) and diallyl ether (0.49 g, 5.0 mmol) in 1 M HC1 (10 mL) at 25°C with vigorous stirring. Extractive work up (ethyl acetate and brine) followed by purification by silica gel column chromatography gave 9 (0.22 g) in 71% yield.