Surprisingly efficient catalytic Cr-mediated coupling reactions

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5421-5424

  Namba, Kosuke ^a   Wang, Jiashi ^a   Cui, Sheng ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHROMIUM; NICKEL;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKYLATION; CATALYSIS; CHROMIUM; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NICKEL;

EID: 28844477490     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052085k     Document Type: Article

References (47)

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19. For X-ray structures of Ni(II)-(1,10-phenanthroline) and Ni(II)-(2,9-dimethyl-1,10-phenanthroline), see, for example: (a) Liu, H.; Liu, L.; Zhong, B. X-ray Struct. Anal. Online 2004, 20, X63.
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26. 2O (Figure 4), see ref 22.
27. Three additional aldehydes a-c were tested under the same conditions, where a and b gave equally good results, but the coupling rate with c was much slower. (Chemical Equation Presented)
28. For stoichiometric Fe- or Co/Cr-mediated alkylation, see: Takai, K.; Nitta, K.; Fujimura, O.; Utimoto, K. J. Org. Chem. 1989, 54, 4732.
29. For catalytic Co- or Fe/Cr-mediated haloallylation, see: Kurosu, M.; Lin, M.-H.; Kishi, Y. J. Am. Chem. Soc. 2004, 126, 12248.
30. 2 (58 mg, 2.0 mmol) in DME (0.25 mL) were added 1 (27 μL, 0.2 mmol) and 1-iodohexane (85 mg, 0.4 mmol). The mixture was stirred for 6 h at room temperature, diluted with ethyl acetate (10 mL), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (elution with hexanes/ethyl acetate = 19/1 to 9/1) to give 2-butyl-5-phenylpent-1 -en-3-ol (39 mg, 89%) as a colorless oil.
31. For Cr-mediated propargylation, see: (a) Inoue, M.; Nakada, M. Organic Lett. 2004, 6, 2977.
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35. For stoichiometric Cr-mediated allylation, see: Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179.
36. Okude, Y.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1977, 43, 3829.
37. For Cr-mediated catalytic asymmetric allylations, see: (a) Sugimoto, K.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1997, 62, 2322.
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41. (e) See ref 6a.
42. (f) Lee, J.; Miller, J. J.; Hamilton, S. S.; Sigtnan, M. S. Org. Lett. 2005, 7, 1837.
43. 2 (47 mg, 0.16 mmol) in DME (0.25 mL) were added 1 (27 μL, 0.20 mmol) and allyl bromide (43 μL, 0.50 mmol). The mixture was stirred for 2 h at room temperature, diluted with ethyl acetate (10 mL), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (elution with hexanes/ethyl acetate = 19/1 to 9/1) to give 2-butyl-5-phenylpent-1-en-3-ol (32 mg, 9%) as a colorless oil.
44. (a) Catalyst loads used for common cross-couplings are typically in the following range: Heck coupling, 1-10 mol %; Hiyama coupling, 1-5 mol %; Kumada coupling, 0.1-3 mol %; Negishi coupling, 3-10 mol %; Sonogashira coupling, 2-10 mol % and the lowest reported is 0.0001 mol %; Stille coupling, 1-5 mol %; Suzuki-Miyaura coupling, 0.5-5 mol % and the lowest reported is 0.0001 mol %. See a review: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176 and references therein.
45. (b) Catalyst loads used for metathesis are typically in the range of 5-10 mol %, and the lowest reported is 1 mol %. See a review: Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490 and references therein.
46. Namba, K.; Kishi, Y. J. Am. Chem. Soc. 2005, 127, in press.
47. 3-3THF (411 mg, 1.1 mmol) in MeCN (3 mL) was sonicated for 1 min, shaken until the color of the solution changed from light purple to dark green, and concentrated under reduced pressure. The residue was taken up with hot THF (50 mL). The resultant cloudy solution was filtered through Celite and concentrated down to half its volume. Then, the vapor diffusion technique was applied: the THF solution in an open vial was placed in a closed pentane chamber for 24 h to give dark green crystals. The supernatant was discarded, and the crystals were washed with pentane (x3) and dried under reduced pressure to give the Cr complex (300 mg, 58%). A single crystal was grown from THF-pentane. An X-ray analysis showed that this crystal contains one water molecule; see Figure 4.