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
. 2014 Apr 25;53(18):4667-70.
doi: 10.1002/anie.201311029. Epub 2014 Mar 25.

Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation

Stacey L McDonald  1 , Charles E Hendrick, Qiu Wang
Affiliations

Copper-catalyzed electrophilic amination of heteroarenes and arenes by C-H zincation

Stacey L McDonald et al. Angew Chem Int Ed Engl. .

Abstract

Direct amination of heteroarenes and arenes has been achieved in a one-pot CH zincation/copper-catalyzed electrophilic amination procedure. This amination method provides an efficient and rapid approach to access a diverse range of heteroaromatic and aromatic amines including those previously inaccessible using CH amination methods. The mild reaction conditions and good functional-group compatibility demonstrate its great potential for the synthesis of important and complex amines.

Keywords: CH functionalization; amination; copper; heterocycles; synthetic methods.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Selected examples of bioactive heteroaromatic amines.
Scheme 1
Scheme 1
Direct C–H amination to access heteroaromatic amines. Bz= benzoyl, TEMPO= 2,2,6,6-tetramethyl-1-piperidinyloxy.
Scheme 2
Scheme 2
A rapid synthesis of lerisetron.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Orjales A, Mosquera R, Labeaga L, Rodes R. J. Med. Chem. 1997;40:586. - PubMed
    2. Jin CY, Burgess JP, Rehder KS, Brine GA. Synthesis. 2007:219.
    3. Eckhardt M, Langkopf E, Mark M, Tadayyon M, Thomas L, Nar H, Pfrengle W, Guth B, Lotz R, Sieger P, Fuchs H, Himmelsbach F. J. Med. Chem. 2007;50:6450. - PubMed
    4. Massari S, Daelemans D, Barreca ML, Knezevich A, Sabatini S, Cecchetti V, Marcello A, Pannecouque C, Tabarrini O. J. Med. Chem. 2010;53:641. - PubMed
    5. Gallardo-Godoy A, Gever J, Fife KL, Silber BM, Prusiner SB, Renslo AR. J. Med. Chem. 2011;54:1010. - PMC - PubMed
    6. Zhang TZ, Yan ZH, Sromek A, Knapp BI, Scrimale T, Bidlack JM, Neumeyer JL. J. Med. Chem. 2011;54:1903. - PMC - PubMed
    7. Bansal Y, Silakari O. Bioorg. Med. Chem. 2012;20:6208. - PubMed
    8. Zimmermann G, Papke B, Ismail S, Vartak N, Chandra A, Hoffmann M, Hahn SA, Triola G, Wittinghofer A, Bastiaens PI, Waldmann H. Nature. 2013;497:638. - PubMed
    1. Paul F, Patt J, Hartwig JF. J. Am. Chem. Soc. 1994;116:5969.
    2. Guram AS, Buchwald SL. J. Am. Chem. Soc. 1994;116:7901.
    3. Hooper MW, Utsunomiya M, Hartwig JF. J. Org. Chem. 2003;68:2861. - PubMed
    4. Charles MD, Schultz P, Buchwald SL. Org. Lett. 2005;7:3965. - PubMed
    1. Kim HJ, Kim J, Cho SH, Chang S. J. Am. Chem. Soc. 2011;133:16382. - PubMed
    2. Lamani M, Prabhu KR. J. Org. Chem. 2011;76:9552. - PubMed
    3. Wertz S, Kodama S, Studer A. Angew. Chem. 2011;123:11713. - PubMed
    4. Angew. Chem. Int. Ed. 2011;50:11511.
    5. Yotphan S, Beukeaw D, Reutrakul V. Synthesis. 2013;45:936.
    1. Armstrong A, Collins JC. Angew. Chem. 2010;122:2332. - PubMed
    2. Angew. Chem. Int. Ed. 2010;49:2282.
    3. Monguchi D, Fujiwara T, Furukawa H, Mori A. Org. Lett. 2009;11:1607. - PubMed
    4. Wang Q, Schreiber SL. Org. Lett. 2009;11:5178. - PMC - PubMed
    5. Kawano T, Hirano K, Satoh T, Miura M. J. Am. Chem. Soc. 2010;132:6900. - PubMed
    6. Matsuda N, Hirano K, Satoh T, Miura M. Org. Lett. 2011;13:2860. - PubMed
    7. Li Y, Xie Y, Zhang R, Jin K, Wang X, Duan C. J. Org. Chem. 2011;76:5444. - PubMed
    8. Kienle M, Wagner AJ, Dunst C, Knochel P. Chem. Asian J. 2011;6:517. - PubMed
    9. Mitsuda S, Fujiwara T, Kimigafukuro K, Monguchi D, Mori A. Tetrahedron. 2012;68:3585.
    10. Wagh YS, Bhanage BM. Tetrahedron Lett. 2012;53:6500.
    11. Xu J, Li JR, Wei Z, Zhang Q, Shi DX. RSC Adv. 2013;3:9622.
    12. Boudet N, Dubbaka SR, Knochel P. Org. Lett. 2008;10:1715. - PubMed
    1. Yoo EJ, Ma S, Mei T-S, Chan KSL, Yu J-Q. J. Am. Chem. Soc. 2011;133:7652. - PubMed
    2. Ng KH, Chan ASC, Yu WY. J. Am. Chem. Soc. 2010;132:12862. - PubMed
    3. Ng KH, Ng FN, Yu WY. Chem. Commun. 2012;48:11680. - PubMed
    4. Dong Z, Dong G. J. Am. Chem. Soc. 2013;135:18350. - PubMed
    5. Cho SH, Kim JY, Lee SY, Chang S. Angew. Chem. 2009;121:9291. - PubMed
    6. Angew. Chem. Int. Ed. 2009;48:9127.
    7. Grohmann C, Wang HG, Glorius F. Org. Lett. 2012;14:656. - PubMed
    8. Ng K-H, Zhou Z, Yu W-Y. Org. Lett. 2012;14:272. - PubMed
    9. Kim JY, Park SH, Ryu J, Hwan S, Kim SH, Chang S. J. Am. Chem. Soc. 2012;134:9110. - PubMed
    10. Grohmann C, Wang H, Glorius F. Org. Lett. 2013;15:3014. - PubMed
    11. Shin K, Baek Y, Chang S. Angew. Chem. 2013;125:8189. - PubMed
    12. Angew. Chem. Int. Ed. 2013;52:8031.
    13. Tang RJ, Luo CP, Yang L, Li CJ. Adv. Synth. Catal. 2013;355:869.
    14. Yu S, Wan B, Li X. Org. Lett. 2013;15:3706. - PubMed
    15. Thirunavukkarasu VS, Raghuvanshi K, Ackermann L. Org. Lett. 2013;15:3286. - PubMed
    16. Wang JA, Hou JT, Wen J, Zhang J, Yu XQ. Chem. Commun. 2011;47:3652. - PubMed

Publication types

LinkOut - more resources