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. 2013;24(14):1842-1844.
doi: 10.1055/s-0033-1339510.

Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes

Todd K Hyster  1 , Tomislav Rovis  1
Affiliations

Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes

Todd K Hyster et al. Synlett. 2013.

Abstract

We have developed a synthesis of 4-substituted isoquinolones from the Rh(III)-catalyzed, C-H activation mediated, coupling of O-pivaloyl benzhydroxamic acids and 3,3-disubstituted cyclopropenes. Experiments suggest the formation of a [4.1.0] bicyclic-system, which can open under acidic conditions to generate the desired isoquinolone.

Keywords: C–H activation; cyclopropene; donor-acceptor cyclopropane; heterocycles; isoquinolone.

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Figures

Figure 1
Figure 1
Proposed approach to access mono-substituted isoquinolones
Scheme 1
Scheme 1
mono-activated cyclopropenes
Scheme 2
Scheme 2
Cyclopropane Opening
See this image and copyright information in PMC

References

    1. For a review of isoquinolone synthesis; see: Glushkov VA, Shklyaev YV. Chem. Heterocycl. Compd. 2001;37:663.

    1. Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010;132:6908. - PubMed
    2. Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010;39:744.
    3. Hyster TK, Rovis T. J. Am. Chem. Soc. 2010;132:10565. - PMC - PubMed
    4. Song G, Chen D, Pan C-L, Crabtree RH, Li X. J. Org. Chem. 2010;75:7487. - PubMed
    5. Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011;133:6449. - PubMed
    6. Wang H, Grohmann C, Nimphius C, Glorius F. J. Am. Chem. Soc. 2012;134:19592. - PubMed
    1. Reissig H-U, Zimmer R. Chem. Rev. 2003;103:1151. - PubMed
    2. Yu M, Pagenkopf BL. Tetrahedron. 2005;61:321.
    3. Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007;107:3117. - PubMed
    4. Carson CA, Kerr MA. Chem. Soc. Rev. 2009;38:3051. - PubMed
    5. De Simone F, Waser J. Synthesis. 2009:3353.
    6. Campbell MJ, Johnson JS, Parsons AT, Pohlhaus PD, Sanders SD. J. Org. Chem. 2010;75:6317. - PubMed
    1. De Simone F, Waser J. Synlett. 2009:593.
    2. De Simone F, Gertsch J, Waser J. Angew. Chem. Int. Ed. 2010;49:5767. - PubMed
    3. de Nanteuil F, Waser J. Angew. Chem. Int. Ed. 2011;50:12075. - PubMed
    4. Benfatti F, de Nanteuil F, Waser J. Org. Lett. 2012;14:386. - PubMed
    5. Benfatti F, de Nanteuil F, Waser J. Chem. Eur. J. 2012;18:4844. - PubMed
    1. Rakshit S, Grohmann C, Besset T, Glorius F. J. Am. Chem. Soc. 2011;133:2350. - PubMed
    2. Wang H, Glorius F. Angew. Chem. Int. Ed. 2012;51:7318. - PubMed

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