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. 2011 Nov 28;47(44):12074-6.
doi: 10.1039/c1cc15843k. Epub 2011 Oct 17.

Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide

Ya Du  1 , Todd K Hyster, Tomislav Rovis
Affiliations

Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide

Ya Du et al. Chem Commun (Camb). .

Abstract

An efficient strategy for the oxidative carbonylation of aromatic amides via C-H/N-H activation to form phthalimides using an Rh(III) catalyst has been developed. The reaction shows a preference for C-H bonds of electron-rich aromatic amides and tolerates a variety of functional groups.

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Figures

Figure 1
Figure 1
Reversible C–H activation
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
Chart 1
Chart 1
Reaction Scope
See this image and copyright information in PMC

References

    1. Kollár L. Modern Carbonylation Methods. Wiley-VCH; Weinheim: 2008.
    1. Schoenberg A, Bartoleti I, Heck RF. J Org Chem. 1974;39:3318.
    2. Schoenberg A, Heck RF. J Org Chem. 1974;39:3327.
    3. Giri R, Yu JQ. J Am Chem Soc. 2008;130:14082. - PubMed
    4. Giri R, Lam JK, Yu JQ. J Am Chem Soc. 2010;132:686. - PubMed
    5. Haffemayer B, Gaunt MJ. Chem Sci. 2011;2:312.
    6. Lu Y, Leow D, Wang X, Engle KM, Yu JQ. Chem Sci. 2011;2:967.

    1. During the preparation of this manuscript, a related Pd(II) catalyzed carbonylation of N-alkoxybenzamides was reported. See: Wrigglesworth JW, Cox B, Lloyd-Jones GC, Booker-Milburn KI. Org Lett. 2011;13 doi: 10.10211/ol202187h.

    1. Mägerlein W, Indolese AF, Beller M. Angew Chem, Int Ed. 2001;40:2856. and references cited in. - PubMed
    1. Munday RH, Martinelli JR, Buchwald SL. J Am Chem Soc. 2008;130:2754. and references cited in. - PubMed

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