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
. 2008 Jan 30;130(4):1128-9.
doi: 10.1021/ja077862l. Epub 2008 Jan 9.

Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds

Hien-Quang Do  1 , Olafs Daugulis
Affiliations

Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds

Hien-Quang Do et al. J Am Chem Soc. .

Abstract

An efficient, copper-catalyzed method for the arylation, alkenylation, and benzylation of polyfluoroarenes has been developed. Arenes containing two or more fluorine substituents on the aromatic ring can be efficiently functionalized. The best results are obtained by using a combination of copper iodide catalyst, phenanthroline ligand, aryl bromide or aryl iodide coupling partner and DMF or DMF/xylene mixed solvent.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Mechanistic considerations.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Oi S, Fukita S, Hirata N, Watanuki N, Miyano S, Inoue Y. Org Lett. 2001;3:2579. - PubMed
    2. Oi S, Ogino Y, Fukita S, Inoue Y. Org Lett. 2002;4:1783. - PubMed
    3. Ackermann L. Org Lett. 2005;7:3123. - PubMed
    4. Bedford RB, Coles SJ, Hursthouse MB, Limmert ME. Angew Chem, Int Ed. 2003;42:112. - PubMed
    5. Kametani Y, Satoh T, Miura M, Nomura M. Tetrahedron Lett. 2000;41:2655.
    6. Kalyani D, Deprez NR, Desai LV, Sanford MS. J Am Chem Soc. 2005;127:7330. - PubMed
    7. Satoh T, Kawamura Y, Miura M, Nomura M. Angew Chem, Int Ed. 1997;36:1740.
    8. Chen X, Li JJ, Hao XS, Goodhue CE, Yu JQ. J Am Chem Soc. 2006;128:78. - PubMed
    9. Chen X, Goodhue CE, Yu JQ. J Am Chem Soc. 2006;128:12634. - PubMed
    10. Motti E, Faccini F, Ferrari I, Catellani M, Ferraccioli R. Org Lett. 2006;8:3967. - PubMed
    11. Lewis JC, Wiedemann SH, Bergman RG, Ellman JA. Org Lett. 2004;6:35. - PubMed
    12. Seregin IV, Gevorgyan V. Chem Soc Rev. 2007;36:1173. - PMC - PubMed
    13. Alberico D, Scott ME, Lautens M. Chem Rev. 2007;107:174. - PubMed
    1. Fujita K-i, Nonogawa M, Yamaguchi R. Chem Commun. 2004:1926. - PubMed
    2. Fuchita Y, Oka H, Okamura M. Inorg Chim Acta. 1992;194:213.
    3. Tani M, Sakaguchi S, Ishii Y. J Org Chem. 2004;69:1221. - PubMed
    4. Jintoku T, Fujiwara Y, Kawata I, Kawauchi T, Taniguchi H. J Organomet Chem. 1990;385:297.
    5. Ackerman LJ, Sadighi JP, Kurtz DM, Labinger JA, Bercaw JE. Organometallics. 2003;22:3884.
    6. Proch S, Kempe R. Angew Chem, Int Ed. 2007;46:3135. - PubMed
    7. Hull KL, Sanford MS. J Am Chem Soc. 2007;129:11904. - PubMed
    1. Lafrance M, Rowley CN, Woo TK, Fagnou K. J Am Chem Soc. 2006;128:8754. - PubMed
    2. Lafrance M, Shore D, Fagnou K. Org Lett. 2006;8:5097. - PubMed

    1. Copper-catalyzed C-N and C-C bond formation: Klapars A, Antilla JC, Huang X, Buchwald SL. J Am Chem Soc. 2001;123:7727.Allred GD, Liebeskind LS. J Am Chem Soc. 1996;118:2748.Thathagar MB, Beckers J, Rothenberg G. J Am Chem Soc. 2002;124:11858.Ma D, Liu F. Chem Commun. 2004:1934.del Amo V, Dubbaka SR, Krasovskiy A, Knochel P. Angew Chem, Int Ed. 2006;45:7838.Campbell MJ, Johnson JS. Org Lett. 2007;9:1521.Schaub T, Backes M, Radius U. J Am Chem Soc. 2006;128:15964.

    1. Chen X, Hao XS, Goodhue CE, Yu JQ. J Am Chem Soc. 2006;128:6790. - PubMed
    2. Uemura T, Imoto S, Chatani N. Chem Lett. 2006;35:842.
    3. Li Z, Li CJ. J Am Chem Soc. 2005;127:6968. - PubMed

Publication types