Ruthenium-catalyzed conversion of sp3 C-O bonds in ethers to C-C bonds using triarylboroxines

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3254-3257

  Ogiwara, Yohei ^a   Kochi, Takuya ^a   Kakiuchi, Fumitoshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79958822320     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2012007     Document Type: Article

References (46)

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34. Detailed results are shown in the Supporting Information (Table S1).
35. After the optimization of conditions, catalysts used for entry 2-5, Table 1, were again tested for the reaction, but only low yields of product 2aa were obtained.
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43. Vinylpyridine 10 was not observed when the reaction was performed without either 3 and 5a. Heating ether 1d in toluene at 120 °C also failed to give 10. These results suggest both ruthenium complex 3 and boronate 5a are required for efficient formation of vinylpyridine intermediate 10.
44. 3 position was also observed for the reaction of vinylpyridine 10 with 5a. See the Supporting Information for details.
45. 2 positions was supported by the result that deuterium incorporation at these positions was observed for 2da when the reaction of 1d with 5d was performed in the presence of 2da. See the Supporting Information for details.
46. 1H NMR spectrum of a mixture of 1d and boroxine 5a also showed a significant low-field shift (0.26 ppm) of the pyridyl proton at the 6-position as well as high-field shifts of the protons around the etheral oxygen up to 0.09 ppm. The results suggest that both the nitrogen and the oxygen of substrate 1d can interact with the ruthenium catalyst or boroxines under the conditions for the catalytic reaction.