Rhodium(l)-catalyzed carbonyl allenylation versus propargylation via redox transmetalation across tetragonal tin(ll) oxide

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2137-2140

  Banerjee, Moloy ^a   Roy, Sujit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; OXIDE; RHODIUM; TIN;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; METAL BINDING; OXIDATION REDUCTION REACTION; PHASE TRANSITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 3142656623     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0493352     Document Type: Article

References (22)

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5. For allylic, aryl, and propargylic activation by Rh(I) complexes, see: (a) Chin, C. S.; Shin, S. Y.; Lee, C. J. Chem. Soc., Dalton Trans. 1992, 1323. (b) Li, C. J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (c) Kayan, A.; Gallucci, J. C.; Wojcicki, A. J. Organomet. Chem. 2001, 630, 44.
6. For allylic, aryl, and propargylic activation by Rh(I) complexes, see: (a) Chin, C. S.; Shin, S. Y.; Lee, C. J. Chem. Soc., Dalton Trans. 1992, 1323. (b) Li, C. J.; Meng, Y. J. Am. Chem. Soc. 2000, 122, 9538. (c) Kayan, A.; Gallucci, J. C.; Wojcicki, A. J. Organomet. Chem. 2001, 630, 44.
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11. Earlier attempts in this regard have been to vary process parameters such as temperature, solvent, or additive or to execute a further transmetalation involving tin-tin, tin-indium, tin-lithium, and tin-boron. See: (a) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (c) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696. (d) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (e) Corey, E. J.; Yu, C. M.; Lee, D. H. J. Am. Chem. Soc. 1990, 112, 878.
12. Earlier attempts in this regard have been to vary process parameters such as temperature, solvent, or additive or to execute a further transmetalation involving tin-tin, tin-indium, tin-lithium, and tin-boron. See: (a) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (c) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696. (d) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (e) Corey, E. J.; Yu, C. M.; Lee, D. H. J. Am. Chem. Soc. 1990, 112, 878.
13. Earlier attempts in this regard have been to vary process parameters such as temperature, solvent, or additive or to execute a further transmetalation involving tin-tin, tin-indium, tin-lithium, and tin-boron. See: (a) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (c) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696. (d) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (e) Corey, E. J.; Yu, C. M.; Lee, D. H. J. Am. Chem. Soc. 1990, 112, 878.
14. Earlier attempts in this regard have been to vary process parameters such as temperature, solvent, or additive or to execute a further transmetalation involving tin-tin, tin-indium, tin-lithium, and tin-boron. See: (a) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (c) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696. (d) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (e) Corey, E. J.; Yu, C. M.; Lee, D. H. J. Am. Chem. Soc. 1990, 112, 878.
15. Earlier attempts in this regard have been to vary process parameters such as temperature, solvent, or additive or to execute a further transmetalation involving tin-tin, tin-indium, tin-lithium, and tin-boron. See: (a) Masuyama, Y.; Watabe, A.; Ito, A.; Kurusu, Y. Chem. Commun. 2000, 2009. (b) Marshall, J. A.; Yu, R. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550. (c) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696. (d) Suzuki, M.; Morita, Y.; Noyori, R. J. Org. Chem. 1990, 55, 441. (e) Corey, E. J.; Yu, C. M.; Lee, D. H. J. Am. Chem. Soc. 1990, 112, 878.
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18. 4F (15%, 10 mL) was added to the reaction mixture, and the organic layer was extracted with diethyl ether (3 x 10 mL), washed with water (2 x 10 mL) and brine (2 x 10 mL), and dried over magnesium sulfate. Solvent removal followed by column chromatography (eluent n-hexanes-ethyl acetate; gradient elution) afforded pure 1-(4-chloro-phenyl)-2-phenyl-buta-2,3-dien-1-ol (99 mg, 77% with respect to aldehyde).
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