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 23;133(46):18566-9.
doi: 10.1021/ja208068w. Epub 2011 Nov 2.

Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis

Affiliations

Room-temperature C-H arylation: merger of Pd-catalyzed C-H functionalization and visible-light photocatalysis

Dipannita Kalyani et al. J Am Chem Soc. .

Abstract

This communication describes the development of a room-temperature ligand-directed C-H arylation reaction using aryldiazonium salts. This was achieved by the successful merger of palladium-catalyzed C-H functionalization and visible-light photoredox catalysis. The new method is general for a variety of directing groups and tolerates many common functional groups.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Possible Mechanism for Pd/Ru-Catalyzed C–H Arylation Reactions
Scheme 1
Scheme 1
Pd-Catalyzed C–H Arylation with Diaryliodonium Salts
Scheme 2
Scheme 2
Background Reactions with Electron Deficient Aryldiazonium Salts

References

    1. Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002;102:1359. - PubMed
    1. For representative reviews on C–H arylation, see: Alberico D, Scott ME, Lautens M. Chem. Rev. 2007;107:174. Kakiuchi F, Kochi T. Synthesis. 2008:3013. McGlacken GP, Bateman L. Chem. Soc. Rev. 2009;38:2447. Chen X, Engle KM, Wang D-H, Yu J-Q. Angew. Chem. Int. Ed. 2009;48:5094. Lyons TW, Sanford MS. Chem. Rev. 2010;110:1147. Daugulis O. Top. Curr. Chem. 2010;292:57. Chiusoli GP, Catellani M, Costa M, Motti E, Ca’ ND, Maestri G. Coord. Chem. Rev. 2010;254:456.

    1. Wencel-Delord J, Droge T, Liu F, Glorius F. Chem. Soc. Rev. 2011;40:4740. - PubMed
    1. For isolated examples of room temperature Pd-catalyzed C–H arylation, see: Hull KL, Lanni EL, Sanford MS. J. Am. Chem. Soc. 2006;128:14047. Xiao B, Fu Y, Xu J, Gong T-J, Dai J-J, Yi J, Liu L. J. Am. Chem. Soc. 2010;132:468. Nishikata T, Abela AR, Huang S, Lipshutz BH. J. Am. Chem. Soc. 2010;132:4978. Nishikata T, Abela AR, Lipshutz BH. Angew. Chem. Int. Ed. 2010;49:781. Haffemayer B, Gulias M, Gaunt MJ. Chem. Sci. 2011;2:312. Tredwell MJ, Gulias M, Bremeyer N, Johansson CCC, Collins BSL, Gaunt MJ. Angew. Chem. Int. Ed. 2011;50:1076.

    1. Kalyani D, Deprez NR, Desai LV, Sanford MS. J. Am. Chem. Soc. 2005;127:7330. - PubMed

Publication types