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. 2010 Dec 15;132(49):17378-80.
doi: 10.1021/ja108754f. Epub 2010 Nov 17.

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

Eun Jeong Yoo  1 , Masayuki Wasa, Jin-Quan Yu
Affiliations

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

Eun Jeong Yoo et al. J Am Chem Soc. .

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.

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Figures

Figure 1
Figure 1
Natural products that contain 1,4-dicarbonyl moieties.
Scheme 1
Scheme 1
Ring Opening of Succinimides
See this image and copyright information in PMC

References

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    1. For recent reports describing the synthesis of 1,4-dicarbonyl compounds, see: Jang H-Y, Hong J-B, MacMillan DWC. J. Am. Chem. Soc. 2007;129:7004. DeMartino MP, Chen K, Baran PS. J. Am. Chem. Soc. 2008;130:11546. Liu Q, Perreault S, Rovis T. J. Am. Chem. Soc. 2008;130:14066.

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