Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Nov 4;17(45):12591-5.
doi: 10.1002/chem.201102475. Epub 2011 Oct 4.

Rhodium-catalyzed annulation of N-benzoylsulfonamide with isocyanide through C-H activation

Chen Zhu  1 , Weiqing Xie, John R Falck
Affiliations

Rhodium-catalyzed annulation of N-benzoylsulfonamide with isocyanide through C-H activation

Chen Zhu et al. Chemistry. .

Abstract

Isocyanide insertion: the first rhodium-catalyzed annulation of N-benzoylsulfonamide incorporating with isocyanide via C-H activation is described. The transformation is broadly compatible with N-benzoylsulfonamides bearing various electron-properties as well as isocyanides. From practical point of view, this methodology provides the most straightforward approach to a series of 3-(imino)isoindolinones.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Plausible Mechanism
Figure 2
Figure 2
Steric Influence of Isocyanide on Isomer Ratio
Scheme 1
Scheme 1
Annulation with C1 Source via C-H Activation
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For recent reviews: Chen X, Engle KM, Wang D-H, Yu J-Q. Angew. Chem., Int. Ed. 2009;48:5094. Daugulis O, Do H-Q, Shabashov D. Acc. Chem. Res. 2009;42:1074. Giri R, Shi B-F, Engle KM, Maugel N, Yu J-Q. Chem. Soc. Rev. 2009;38:3242. Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010;110:624. Lyons TW, Sanford MS. Chem. Rev. 2010;110:1147. Ackermann L. Chem. Commun. 2010;46:4866. Jazzar R, Hitce J, Renaudat A, Sofack-Kreutzer J, Baudoin O. Chem. Eur. J. 2010;16:2654. Yeung CS, Dong VM. Chem. Rev. 2011;111:1215. and references cited therein.

    1. For examples using alkenes: Miura M, Tsuda T, Satoh T, Pivsa-Art S, Nomura M. J. Org. Chem. 1998;63:5211. Houlden CE, Bailey CD, Ford JG, Gagné MR, Lloyd-Jones GC, Booker-Milburn KI. J. Am. Chem. Soc. 2008;130:10066. Li J-J, Mei T-S, Yu J-Q. Angew. Chem., Int. Ed. 2008;47:6452. Wasa M, Engle KM, Yu J-Q. J. Am. Chem. Soc. 2010;132:3680. Wang F, Song G, Li X. Org. Lett. 2010;12:5430. Rakshit S, Grohmann C, Besset T, Glorius F. J. Am. Chem. Soc. 2011;133:2350.

    1. For examples using alkynes: Stuart DR, Bertrand-Laperle M, Burgess KMN, Fagnou K. J. Am. Chem. Soc. 2008;130:16474. Guimond N, Gouliaras C, Fagnou K. J. Am. Chem. Soc. 2010;132:6908. Rakshit S, Patureau FW, Glorius F. J. Am. Chem. Soc. 2010;132:9585. Hyster TK, Rovis T. J. Am. Chem. Soc. 2010;132:10565. Stuart DR, Alsabeh P, Kuhn M, Fagnou K. J. Am. Chem. Soc. 2010;132:18326. Mochida S, Umeda N, Hirano K, Satoh T, Miura M. Chem. Lett. 2010;39:744. Song G, Chen D, Pan C-L, Crabtree RH, Li X. J. Org. Chem. 2010;75:7487. Su Y, Zhao M, Han K, Song G, Li X. Org. Lett. 2010;12:5462. Ackermann L, Lygin AV, Hofmann N. Org. Lett. 2011;13:3278. Ackermann L, Lygin AV, Hofmann N. Angew. Chem., Int. Ed. 2011;50:6379. Guimond N, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2011;133:6449.

    1. Inoue S, Shiota H, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2009;131:6898. - PubMed
    2. Yoo EJ, Wasa M, Yu J-Q. J. Am. Chem. Soc. 2010;132:17378. - PMC - PubMed
    3. Hasegawa N, Charra V, Inoue S, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011;133:8070. - PubMed

    1. For recent reviews: Dömling A. Chem. Rev. 2006;106:17. Kaim LE, Grimaud L. Tetrahedron. 2009;65:2153. Banfi L, Riva R, Basso A. Synlett. 2010:23. Lygin AV, de Meijere A. Angew. Chem., Int. Ed. 2010;49:9094. Tobisu M, Chatani N. Chem. Lett. 2011;40:330. and references cited therein.

Publication types

LinkOut - more resources