Nickel-catalyzed alkylation of aldehydes with trialkylboranes

Organic Letters

Volumn 7, Issue 21, 2005, Pages 4689-4691

  Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BORANE DERIVATIVE; NICKEL;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALKYLATION; BORANES; CATALYSIS; MOLECULAR STRUCTURE; NICKEL;

EID: 27144490056     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051917b     Document Type: Article

References (12)

1. Mikhailov, B. M.; Baryshnikova, T. K.; Shashkov, A. S. J. Organomet. Chem. 1981, 219, 301-308.
2. Kabalka, G. W.; Wu, Z.; Trotman, S. E.; Gao, X. Org. Lett. 2000, 2, 255-256.
3. Additions of trialkylboranes under electrochemical and free radical conditions were reported: (a) Choi, J. H.; Youm, J. S.; Cho, C.; Czae, M.; Hwang, B. K.; Kim, J. S. Tetrahedron Lett. 1989, 39, 4835-4838.
4. (b) Miyaura, N.; Itoh, M.; Suzuki, A.; Brown, H. C.; Midland, M. M.; Jacob, P. J. Am. Chem. Soc. 1972, 94, 6549-6550.
5. Burguete, M. I.; Collado, M.; Escorihuela, J.; Galindo, F.; García-verdugo, E.; Luis, S. V.; Vicent, M. J. Tetrahedron Lett. 2003, 44, 6891-6894.
6. (a) Ichiyanagi, T.; Kuniyama, S.; Shimizu, M.; Fujisawa, T. Chem. Lett. 1998, 1033-1034.
7. (b) Biswas, K.; Prieto, O.; Goldsmith, P. J.; Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 2232-2234.
8. Nickel-catalyzed 1,2-addition reactions of aryl- and alkenylboronic ester derivatives have been reported. Takahashi, G.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2005, 1459-1460.
9. 3P were ineffective.
10. The conversion of 1d was low and about 40% of the starting material remained unchanged. The conceivable Suzuki-Miyaura coupling product was obtained in less than 2% yield. The reaction of other electron-deficient aromatic aldehydes also resulted in low conversions. For examples, ethylations of 4-trifluoromethylbenzaldehyde and 4-methoxycarbonylbenzaldehyde provided the corresponding adducts in 49% and 29% yields, respectively.
11. 2-Coordinated nickel complexes with aldehydes have been reported. Ogoshi, S.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802-11803. Although the possibility of a radical pathway cannot be completely excluded, addition of a radical scavenger, TEMPO, gave no effect on yield.
12. 3B, the reduced product 13 was mainly obtained, probably due to considerably rapid β-H elimination from the intermediate corresponding to 9.