Rh-catalyzed reductive coupling reaction of aldehydes with conjugated dienes promoted by triethylborane

Organic Letters

Volumn 11, Issue 17, 2009, Pages 3794-3797

  Kimura, Masanari ^a   Nojiri, Daisuke ^a   Fukushima, Masahiro ^a   Oi, Shuichi ^b   Sonoda, Yusuke ^b   Inoue, Yoshio ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BORANE DERIVATIVE; RHODIUM; TRIETHYLBORANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALCOHOLS; ALDEHYDES; BORANES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHODIUM;

EID: 69449093589     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901527b     Document Type: Article

References (21)

1. (a) Metal Catalyzed Reductive C-C Bond Formation. Topics in Current Chemistry; Krische, M. J., Ed.; Springer-Verlag: Berlin, Heidelberg, 2007; Vol.279.
2. (b) Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
3. (a) Kimura, M.; Ezoe, A.; Mori, M.; Iwata, K.; Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559-8568.
4. (b) Tamaru, Y.; Kimura, M. Org. Synth. 2006, 83, 88-96.
5. (c) Kimura, M.; Ezoe, A.; Tanaka, S.; Tamaru, Y. Angew. Chem., Int. Ed. 2001, 40, 3600-3602.
6. (d) Shibata, K.; Kimura, M.; Shimizu, M.; Tamaru, Y. Org. Lett. 2001, 3, 2181-2183.
7. (e) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, S; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397-400.
8. (f) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033-4034.
9. Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005.
10. (a) Jang, H.- Y.; Krische, M. J. Ace. Chem. Res. 2004, 37, 653-661.
11. (b) Jang, H.- Y.; Huddleston, R. R.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 4074-4077.
12. (a) Tsuji, J.; Hará, M.; Ohno, K. Tetrahedron 1974, 30, 2143-2145.
13. (b) Ojima, I. J. Organomet. Chem. 1977, 134, C1-C5.
14. (c) Ojima, I.; Kumagai, M. J. Organomet. Chem. 1978, 157, 2143-2146.
15. (d) Cornish, A. J.; Lappert, M. F.; MacQuitty, J. J.; Maskell, R. K. J. Organomet. Chem. 1979, 177, 153-161.
16. (e) Satoh, M.; Nomoto, Y.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1989, 30, 3789-3792.
17. (f) Kobayashi, S.; Nishio, K. J. Org. Chem. 1994, 59, 6620-6628.
18. (g) Hayashi, N.; Honda, H.; Yasuda, M.; Shibata, I.; Baba, A. Org. Lett. 2006, 8, 4553-4556.
19. (h) Ru-catalyzed coupling reaction of diene with alcohols: Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338-6339.
20. 2 catalyst and 0.1 equiv of KOH proceeded smoothly. The formation of RhOH active species might be required at the initial stage of the reaction: see footnote in Table 1.
21. 2 and EtLi; see:Kulzick, M.; Price, R. T.; Muetterties, E. L. Organometallics 1982, 1, 1256-1258.