Deoxybenzoins from Stille carbonylative cross-couplings using molybdenum hexacarbonyl

Tetrahedron Letters

Volumn 51, Issue 52, 2010, Pages 6886-6889

  Sävmarker, Jonas ^a   Lindh, Jonas ^a   Nilsson, Peter ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Deoxybenzoins; Molybdenum hexacarbonyl; Palladium; Stille

Indexed keywords

BENZOIN; BENZYL DERIVATIVE; BROMINE DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; CHLORIDE; METHANE; MOLYBDENUM; PALLADIUM;

ADDITION REACTION; ARTICLE; BIOTRANSFORMATION; CARBONYLATION; CATALYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; PURIFICATION; REACTION TIME; STILLE REACTION;

EID: 78650678044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.115     Document Type: Article

References (27)

1. Olivera, R.; SanMartin, R.; Churruca, F.; Dominguez, E. J. Org. Chem. 2002, 67, 7215-7225.
2. Carril, M.; SanMartin, R.; Dominguez, E.; Tellitu, I. Tetrahedron 2006, 63, 690-702.
3. Addinall, C. R.; Major, R. T. J. Am. Chem. Soc. 1933, 55, 2153-2163.
4. Kim, T. Y.; Kim, H. S.; Chung, Y. M.; Kim, J. N. Bull. Korean Chem. Soc. 2000, 21, 673-674.
5. Jawdosiuk, M.; Kmiotek-Skarzynska, I.; Wilczynski, W. Can. J. Chem. 1978, 56, 218-220.
6. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
7. Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676-707.
8. Liu, C.; He, C.; Shi, W.; Chen, M.; Lei, A. Org. Lett. 2007, 9, 5601-5604.
9. Su, W.; Raders, S.; Verkade, J. G.; Liao, X.; Hartwig, J. F. Angew. Chem., Int. Ed. 2006, 45, 5852-5855.
10. Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. J. Org. Chem. 1991, 56, 1445-1453.
11. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217-8225.
12. Enquist, P.-A.; Nilsson, P.; Edin, J.; Larhed, M. Tetrahedron Lett. 2005, 46, 3335-3339.
13. Lindh, J.; Fardost, A.; Almeida, M.; Nilsson, P. Tetrahedron Lett. 2010, 51, 2470-2472.
14. Brennfuehrer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114-4133.
15. Odell, L. R.; Savmarker, J.; Larhed, M. Tetrahedron Lett. 2008, 49, 6115-6118.
16. Wu, X.; Ronn, R.; Gossas, T.; Larhed, M. J. Org. Chem. 2005, 70, 3094-3098.
17. Wannberg, J.; Larhed, M. In Modern Carbonylation Methods: Microwave-promoted Carbonylations; Kollar, L., Ed.; Wiley-VCH: Weinheim, 2008; pp 93-114.
18. Morimoto, T.; Kakiuchi, K. Angew. Chem., Int. Ed. 2004, 43, 5580-5588.
19. Ng, S. M.; Zhao, C.; Lin, Z. J. Organomet. Chem. 2002, 662, 120-129.
20. Carvajal, M. A.; Miscione, G. P.; Novoa, J. J.; Bottoni, A. Organometallics 2005, 24, 2086-2096.
21. Pearson, A. J.; Schoffers, E. Organometallics 1997, 16, 5365-5367.
22. Takaya, J.; Sangu, K.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 7090-7093.
23. Verevkin, S. P.; Krasnykh, E. L.; Wright, J. S. Phys. Chem. Chem. Phys. 2003, 5, 2605-2611.
24. 2 (10 mL) and then washed with 0.1 M NaOH (aq, 10 mL). The organic phase was separated, filtered through Florisil, and concentrated in vacuo. The residue was purified by silica chromatography, eluting with pentane/EtOAc (9:1) to furnish the pure products in the yields specified in Table 1.
25. Wu, X.; Nilsson, P.; Larhed, M. J. Org. Chem. 2005, 70, 346-349.
26. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
27. Lagerlund, O.; Larhed, M. J. Comb. Chem. 2006, 8, 4-6.