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
. 2013 Nov 15;15(22):5842-5.
doi: 10.1021/ol402904d. Epub 2013 Nov 1.

Copper-catalyzed etherification of arene C-H bonds

James Roane  1 , Olafs Daugulis
Affiliations

Copper-catalyzed etherification of arene C-H bonds

James Roane et al. Org Lett. .

Abstract

A method for direct, auxiliary-assisted alkoxylation and phenoxylation of β-sp(2) C-H bonds of benzoic acid derivatives and γ-sp(2) C-H bonds of amine derivatives is reported. The reaction employs (CuOH)2CO3 catalyst, air as an oxidant, phenol or alcohol coupling partner, DMF, pyridine, or DMPU solvent, and K2CO3, tetramethylguanidine, or K3PO4 base at 70-130 °C.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Picolinic Acid Directing Group
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Reviews: Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010;110:624. Ackermann L. Chem. Rev. 2011;111:1315. 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. Alberico D, Scott ME, Lautens M. Chem. Rev. 2007;107:174. Nakamura E, Yoshikai N. J. Org. Chem. 2010;75:6061. Yeung CS, Dong VM. Chem. Rev. 2011;111:1215. Sun C-L, Li B-J, Shi Z-J. Chem. Commun. 2010:677. Li C-J. Acc. Chem. Res. 2009;42:335.

    1. Kulkarni AA, Daugulis O. Synthesis. 2009:4087.
    2. Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011;50:11062. - PubMed
    3. Allen SE, Walvoord RR, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013;113:6234. - PMC - PubMed
    4. Hickman AJ, Sanford MS. Nature. 2012;484:177. - PMC - PubMed
    1. Liu W, Ackermann L. Org. Lett. 2013;15:3484. - PubMed
    2. Shan G, Yang X, Ma L, Rao Y. Angew. Chem. Int. Ed. 2012;51:13070. - PubMed
    3. Gulevich AV, Melkonyan FS, Sarkar D, Gevorgyan V. J. Am. Chem. Soc. 2012;134:5528. - PMC - PubMed
    4. Desai LV, Stowers KJ, Sanford MS. J. Am. Chem. Soc. 2008;130:13285. - PMC - PubMed
    5. Thirunavukkarasu VS, Ackermann L. Org. Lett. 2012;14:6206. - PubMed
    6. Zhang YH, Yu J-Q. J. Am. Chem. Soc. 2009;131:14654. - PubMed
    1. Reinaud O, Capdevielle P, Maumy M. J. Chem. Soc. Chem. Commun. 1990:566.
    2. Chen X, Hao X-S, Goodhue CE, Yu J-Q. J. Am. Chem. Soc. 2006;128:6790. - PubMed
    3. Hong S, Huber SM, Gagliardi L, Cramer CC, Tolman WB. J. Am. Chem. Soc. 2007;129:14190. - PMC - PubMed
    4. Wang W, Luo F, Zhang S, Cheng J. J. Org. Chem. 2010;75:2415. - PubMed
    5. Liu Q, Wu P, Yang Y, Zeng Z, Liu J, Yi H, Lei A. Angew. Chem. Int. Ed. 2012;51:4666. - PubMed
    6. Xu R, Wan J-P, Mao H, Pan Y. J. Am. Chem. Soc. 2010;132:15531. - PubMed
    1. Gallardo-Donaire J, Martin R. J. Am. Chem. Soc. 2013;135:9350. - PubMed
    2. Bhadra S, Dzik WI, Gooßen LJ. Angew. Chem. Int. Ed. 2013;52:2959. - PubMed

Publication types