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 Mar 30;133(12):4243-5.
doi: 10.1021/ja200184b. Epub 2011 Mar 8.

Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates

Thanh Truong  1 , Olafs Daugulis
Affiliations

Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates

Thanh Truong et al. J Am Chem Soc. .

Abstract

A transition-metal-free method for arylation of heterocycle and arene carbon-hydrogen bonds by aryl chlorides and fluorides has been developed. The reactions proceed via aryne intermediates and are highly regioselective with respect to the C-H bond coupling component.

PubMed Disclaimer

References

    1. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem Rev. 2002;102:1359. - PubMed

    1. Selected reviews: Colby DA, Bergman RG, Ellman JA. Chem Rev. 2010;110:624.Ackermann L, Vicente R, Kapdi AR. Angew Chem, Int Ed. 2009;48:9792.Chen X, Engle KM, Wang DH, Yu JQ. Angew Chem, Int Ed. 2009;48:5094.Seregin IV, Gevorgyan V. Chem Soc Rev. 2007;36:1173.Lyons TW, Sanford MS. Chem Rev. 2010;110:1147.Daugulis O, Do HQ, Shabashov D. Acc Chem Res. 2009;42:1074.Alberico D, Scott ME, Lautens M. Chem Rev. 2007;107:174.

    1. Selected examples: Akita Y, Inoue A, Yamamoto K, Ohta A, Kurihara T, Shimizu M. Heterocycles. 1985;23:2327.Catellani M, Chiusoli GP, Ricotti S. J Organomet Chem. 1985;296:C11.Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M. Bull Chem Soc Jpn. 1998;71:467.Rieth RD, Mankad NP, Calimano E, Sadighi JP. Org Lett. 2004;6:3981.Chiong HA, Daugulis O. Org Lett. 2007;9:1449.Liégault B, Petrov I, Gorelsky SI, Fagnou K. J Org Chem. 2010;75:1047.Deprez NR, Kalyani D, Krause A, Sanford MS. J Am Chem Soc. 2006;128:4972.Kakiuchi F, Kan S, Igi K, Chatani N, Murai S. J Am Chem Soc. 2003;125:1698.Oi S, Fukita S, Inoue Y. Chem Commun. 1998:2439.Bedford RB, Coles SJ, Hursthouse MB, Limmert ME. Angew Chem, Int Ed. 2003;42:112.Caron L, Campeau LC, Fagnou K. Org Lett. 2008;10:4533.Cho SH, Hwang SJ, Chang S. J Am Chem Soc. 2008;130:9254.Chen X, Li JJ, Hao XS, Goodhue CE, Yu JQ. J Am Chem Soc. 2006;128:78.Chiong HA, Pham QN, Daugulis O. J Am Chem Soc. 2007;129:9879.Desai LV, Stowers KJ, Sanford MS. J Am Chem Soc. 2008;130:13285.Shi Z, Li B, Wan X, Cheng J, Fang Z, Cao B, Qin C, Wang Y. Angew Chem, Int Ed. 2007;46:5554.

    1. Do HQ, Daugulis O. J Am Chem Soc. 2007;129:12404. - PMC - PubMed
    2. Do HQ, Khan RMK, Daugulis O. J Am Chem Soc. 2008;130:15185. - PMC - PubMed
    3. Yotphan S, Bergman RG, Ellman JA. Org Lett. 2009;11:1511. - PMC - PubMed

    1. Yanagisawa S, Ueda K, Taniguchi T, Itami K. Org Lett. 2008;10:4673.Liu W, Cao H, Zhang H, Zhang H, Chung KH, He C, Wang H, Kwong FY, Lei A. J Am Chem Soc. 2010;132:16737.Shirakawa E, Itoh KI, Higashino T, Hayashi T. J Am Chem Soc. 2010;132:15537.Sun CL, Li H, Yu DG, Yu M, Zhou X, Lu XY, Huang K, Zheng SF, Li BJ, Shi ZJ. Nature Chem. 2010;2:1044.Five-membered ring heterocycle arylation by iodonium salts: Kita Y, Morimoto K, Ito M, Ogawa C, Goto A, Dohi T. J Am Chem Soc. 2009;131:1668.Photochemical arylation: Fagnoni M, Albini A. Acc Chem Rev. 2005;38:713.

Publication types

MeSH terms