Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds

C Jia; D Piao; J Oyamada; W Lu; T Kitamura; Y Fujiwara

doi:10.1126/science.287.5460.1992

Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds

Science. 2000 Mar 17;287(5460):1992-5. doi: 10.1126/science.287.5460.1992.

Authors

C Jia¹, D Piao, J Oyamada, W Lu, T Kitamura, Y Fujiwara

Affiliation

¹ Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fukuoka, 812-8581, Japan.

PMID: 10720319
DOI: 10.1126/science.287.5460.1992

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&cjs0812;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.