Heterogeneous catalysis: Ni/C-catalyzed cross-couplings en route to allylated aromatics: Application to a precursor to coenzyme Q10

Synthesis

Volumn , Issue 14, 2002, Pages 2110-2116

  Lipshutz, Bruce H ^a   Frieman, Bryan ^a   Pfeiffer, Steven S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Allylated aromatics; Cross couplings; Heterogeneous catalysis; Nickel on charcoal

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; CHARCOAL; NICKEL; SYNTHESIS (CHEMICAL);

NATURAL PRODUCTS;

COENZYMES;

AROMATIC COMPOUND; NATURAL PRODUCT; NICKEL; QUINONE DERIVATIVE; UBIDECARENONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0036400334     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34384     Document Type: Article

References (17)

1. Lipshutz, B. H.; Mollard, P.; Pfeiffer, S. S.; Chrisman, W., submitted.
2. For a related study using Ni(0) under homogeneous conditions, see: (a) Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54, 6999. (b) Lipshutz, B. H.; Bulow, G.; Stevens, K. L.; Lowe, R. Tetrahedron 1996, 52, 7265.
3. For a related study using Ni(0) under homogeneous conditions, see: (a) Lipshutz, B. H.; Kim, S.-K.; Mollard, P.; Stevens, K. L. Tetrahedron 1998, 54, 6999. (b) Lipshutz, B. H.; Bulow, G.; Stevens, K. L.; Lowe, R. Tetrahedron 1996, 52, 7265.
4. Lipshutz, B. H. Adv. Synth. Catal. 2001, 343, 313.
5. (a) Lipshutz, B. H.; Blomgren, P. A. J. Am. Chem. Soc. 1999, 121, 5819.
6. (b) Lipshutz, B. H.; Tomioka, T.; Blomgren, P. A.; Sclafani, J. A. Inorg. Chim. Acta 1999, 296, 164.
7. (c) Lipshutz, B. H.; Sclafani, J. A.; Blomgren, P. A. Tetrahedron 2000, 56, 2139.
8. (d) Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492;
9. Angew. Chem. 2000, 112, 4666.
10. (e) Lipshutz, B. H.; Tomioka, T.; Sato, K. Synlett 2001, 970.
11. (a) Van Horn, D. E.; Negishi, E. J. Am. Chem. Soc. 1978, 100, 2252.
12. (b) Negishi, E.; Van Horn, D. E.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639.
13. (c) Matsushita, H.; Negishi, E. Org. Synth. 1984, 63, 31.
14. (d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
15. Lipshutz, B. H.; Tasler, S. Adv. Synth. Catal. 2001, 343, 327.
16. Inductively Coupled Plasma Mass Spectrometry; Montaser, A., Ed.; Wiley-VCH: New York, 1998.
17. Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. in press.