Affiliation:
1. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fukuoka, 812–8581, Japan.
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.
Publisher
American Association for the Advancement of Science (AAAS)
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