Arylation of allylsilanes through rhodium catalysis

Chemistry Letters

Volumn 38, Issue 2, 2009, Pages 186-187

  Omachi, Haruka ^a,b   Itami, Kenichiro ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66549109982     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.186     Document Type: Article

References (17)

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11. The use of allyltrimethylsilane resulted in a complex mixture presumably due to the occurrence of competing desilylation pathways.
12. 3 (0.50mmol), allyltriisopropylsilane (1, 0 mmol), and p-nitrophenyl iodide (0.50 mmol) in dry m-xylene (2.0 mL) was stirred at 120°C for 12 h under argon. After cooling to room temperature, the mixture was subjected to flash silica gel chromatography (EtOAc/hexane) to afford 2 (55%) and 3 (12%)
13. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
14. Pd-catalyzed C-H bond arylation of allylsilanes: a) K. Karabelas, C. Westerlund, A. Hallberg, J. Org. Chem. 1985, 50, 3896.
15. b) K. Olofsson, M. Larhed, A. Hallberg, J. Org. Chem. 1998, 63, 5076.
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17. Under the current Rh-based conditions, other electron-rich alkenes such as vinyl ethers are not applicable. For Pd-catalyzed C-H bond arylation reaction of vinyl ethers, see Ref 9.