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 Jun 23;53(26):6692-5.
doi: 10.1002/anie.201403878. Epub 2014 May 14.

Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides

Affiliations

Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides

Youqian Deng et al. Angew Chem Int Ed Engl. .

Abstract

Diverse 4-aryl-2-quinolinones are prepared from propionamides in one pot by ligand-promoted triple sequential C-H activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new C-C bonds and one C-N bond are formed to rapidly build molecular complexity from propionic acid.

Keywords: C-H activation; amidation; arylation; dehydrogenation; quinolinone.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Biologically active 4-aryl-2-quinolinones.
Scheme 2
Scheme 2
Synthetic applications.
Scheme 3
Scheme 3
Proposed catalytic pathway.

Similar articles

Cited by

References

    1. Chan KSL, Wasa M, Chu L, Laforteza BN, Miura M, Yu J-Q. Nat Chem. 2014;6:146. - PMC - PubMed
    1. He J, Li S, Deng Y, Fu H, Laforteza BN, Spangler JE, Homs A, Yu JQ. Science. 2014;343:1216. - PMC - PubMed
    2. Wasa M, Chan KSL, Zhang XG, He J, Miura M, Yu JQ. J Am Chem Soc. 2012;134:18570. - PMC - PubMed
    1. He J, Wasa M, Chan KSL, Yu JQ. J Am Chem Soc. 2013;135:3387. - PubMed
    2. Wasa M, Engle KM, Yu JQ. J Am Chem Soc. 2009;131:9886. - PMC - PubMed
    1. Xu P-F, Wang W, editors. Catalytic Cascade Reactions. Wiley-VCH; Weinheim: 2013. for selected examples of cascade reactions involving palladium-catalyzed C-H activations, see: Wang GW, Yuan TT, Li DD. Angew Chem. 2011;123:1416.Angew Chem Int Ed. 2011;50:1380.Karthikeyan J, Cheng CH. Angew Chem. 2011;123:10054.Angew Chem Int Ed. 2011;50:9880.Piou T, Neuville L, Zhu J. Angew Chem. 2012;124:11729.Angew Chem Int Ed. 2012;51:11561.Piou T, Bunescu A, Wang Q, Neuville L, Zhu J. Angew Chem. 2013;125:12611.Angew Chem Int Ed. 2013;52:12385.Piou T, Neuville L, Zhu J. Org Lett. 2012;14:3760.

    1. For natural products, see: Kitahara Y, Shimizu M, Kubo A. Heterocycles. 1990;31:2085.Kobayashi Y, Harayama T. Org Lett. 2009;11:1063. and references cited therein.

Publication types