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Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds

Science  17 Mar 2000:
Vol. 287, Issue 5460, pp. 1992-1995
DOI: 10.1126/science.287.5460.1992

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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.

  • * To whom correspondence should be addressed. E-mail: yfujitcf{at}mbox.nc.kyushu-u.ac.jp

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