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Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds
Abstract
Efficient electrophilic metalation of aromatic C–H bonds leading to new C–C bond formation through regio- and stereoselective addition to alkynes and alkenes has been realized by a catalytic amount (0.02 to 5 mole percent) of palladium(II) or platinum(II) compounds in a mixed solvent containing trifluoroacetic acid at room temperature. Various arenes undergo unexpected selective trans hydroarylation to terminal or internal C≡C bonds inter- and intramolecularly with high efficiency (up to a turnover number of 4500 for palladium), especially for electron-rich arenes, giving thermodynamically unfavorable cis-alkenes, and the oxygen- and nitrogen-containing heterocycles. The simplicity, generality, and efficiency of this process should be very attractive to the possible industrial application for the functionalization of arenes.
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Cited by
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Metadata
- Authors
- Jia, C., Piao, D., Oyamada, J., Lu, W., Kitamura, T., & Fujiwara, Y.
- Venue
- Science
- Published
- 2000-03-17
- Volume
- 287
- Issue
- 5460
- Pages
- 1992-1995
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2052130134
- Cited by
- 827
- References
- 0
- FWCI
- 24.98
- Type
- journal article
- Language
- en
- Open access
- closed
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- Jia, C., Piao, D., Oyamada, J., Lu, W., Kitamura, T., & Fujiwara, Y. (2000). Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds. Science. https://doi.org/10.1126/science.287.5460.1992
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