Journal of the American Chemical Society 2010-12-15

Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Eun Jeong Yoo, Masayuki Wasa, Jin-Quan Yu

Index: J. Am. Chem. Soc. 49th ed., 132 , 17378-17380, (2010)

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Abstract

Pd(II)-catalyzed β-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.