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
Review
. 2022 Jun 15;17(12):e202200215.
doi: 10.1002/asia.202200215. Epub 2022 May 3.

Recent Advances in 1,2-Amino(hetero)arylation of Alkenes

Yungeun Kwon  1 , Qiu Wang  1
Affiliations
Review

Recent Advances in 1,2-Amino(hetero)arylation of Alkenes

Yungeun Kwon et al. Chem Asian J. .

Abstract

Alkene amino(hetero)arylation presents a highly efficient and straightforward strategy for direct installation of amino groups and heteroaryl rings across a double bond simultaneously. An extensive array of practical transformations has been developed via alkene difunctionalization approach to access a broad range of medicinally valuable (hetero)arylethylamine motifs. This review presents recent progress in 1,2-amino(hetero)arylation of alkenes organized in three different modes. First, intramolecular transformations employing C, N-tethered alkenes will be introduced. Next, two-component reactions will be discussed with different combination of precursors, N-tethered alkenes and external aryl precursor, C-tethered alkenes and external amine precursor, or C, N-tethered reagents, and alkenes. Last, three-component intermolecular amino(hetero)arylation reactions will be covered.

Keywords: (hetero)arylation; (hetero)arylethylamine; alkenes; amination; catalysis; difunctionalization.

PubMed Disclaimer

Figures

Figure 1.
Figure 1.
Pharmaceutical products containing (hetero)arylethylamine moieties.
Scheme 1.
Scheme 1.
Copper(I)-promoted aminoarylation of oxaziridine-tethered alkenes.
Scheme 2.
Scheme 2.
Stereoselective cyclization of N-benzylalk-4-enylaminyl radicals followed by 1,4-aryl migration.
Scheme 3.
Scheme 3.
Visible light-mediated intramolecular aminoarylation of hydrazones with a pendant alkene.
Scheme 4.
Scheme 4.
Copper-catalyzed intramolecular aminoarylation of alkenes via oxidative cyclization.
Scheme 5.
Scheme 5.
Pd(II)-catalyzed intramolecular aminoarylation of alkenes.
Scheme 6.
Scheme 6.
Pd-catalyzed aminoarylation of alkenes by the Wolfe group.
Scheme 7.
Scheme 7.
Pd(II)/Pd(IV)-catalyzed aminoarylation of alkenes utilizing NSFI.
Scheme 8.
Scheme 8.
Gold-catalyzed intramolecular aminoarylation via bimolecular reductive elimination.
Scheme 9.
Scheme 9.
Gold and photoredox dual-catalyzed aminoarylation of alkenes using aryldiazonium salts.
Scheme 10.
Scheme 10.
Gold-catalyzed aminoarylation involving oxidative addition and π-activation of alkenes.
Scheme 11.
Scheme 11.
Photoredox PCET involved Ni-catalyzed amidoarylation of unactivated alkenes.
Scheme 12.
Scheme 12.
1,2-Aminoarylation of oxime ester-tethered alkenes with organoboron reagents.
Scheme 13.
Scheme 13.
Ni-mediated cascade amidoarylation of oxyamide-tethered alkenes.
Scheme 14.
Scheme 14.
Radical azidoarylation of N-arylacrylamide-tethered alkenes as a rapid access to oxindole synthesis.
Scheme 15.
Scheme 15.
Radical-mediated azidoarylation of activated alkenes through 1,4-arylation and desulfonylation.
Scheme 16.
Scheme 16.
Azido(hetero)arylation of alkenes through distal (hetero)aryl migration.
Scheme 17.
Scheme 17.
Copper-catalyzed aminoheteroarylation of alkenes using O-benzoylhydroxylamines.
Scheme 18.
Scheme 18.
Visible-light mediated aminoarylation with in situ generated N–chloroamines.
Scheme 19.
Scheme 19.
Gold-catalyzed 1,2-aminoarylation of alkenes with external anilines.
Scheme 20.
Scheme 20.
Asymmetric Pd-catalyzed alkene aminoarylation reactions through intermolecular anti-aminopalladation.
Scheme 21.
Scheme 21.
Nickel-catalyzed asymmetric reductive 1,2-aminoarylation.
Scheme 22.
Scheme 22.
Rhodium-catalyzed aminoarylation of alkenes with cyclopentadienyl ligands via C–H activation.
Scheme 23.
Scheme 23.
Indoline synthesis with alkenes and 2-halo-anilines.
Scheme 24.
Scheme 24.
Non-annulative two-component carboamination of alkenes under redox-neutral system.
Scheme 25.
Scheme 25.
Visible-light mediated alkene aminoarylation using arylsulfonylacetamides as bifunctional reagents.
Scheme 26.
Scheme 26.
Visible-light induced regioselective aminopyridylation of alkenes using N-aminopyridinium reagents.
Scheme 27.
Scheme 27.
Pd(II)/Pd(IV)-mediated intermolecular aminoarylation of unactivated alkenes via directed aminopalladation.
Scheme 28.
Scheme 28.
Alcohol-directed, Ni-catalyzed three-component umpolung 1,2-aminoarylation of unactivated alcohols.
Scheme 29.
Scheme 29.
Enantioselective three-component radical cascade reactions by dual photoredox and chiral Brønsted acid catalysis.
Scheme 30.
Scheme 30.
Photoredox-catalyzed intermolecular aminoarylation of alkenes via Ritter-type reaction.
Scheme 31.
Scheme 31.
Cu-catalyzed enantioselective intermolecular aminoarylation of styrenes using N-fluoro-N-alkylsulfonamide.
Scheme 32.
Scheme 32.
Photoredox-catalyzed azidoheteroarylation of activated alkenes.
Scheme 33.
Scheme 33.
Metal-free azidoheteroarylation of alkenes via Minisci reactions.
Scheme 34.
Scheme 34.
Redox-neutral dual catalytic azidoarylation of alkenes.
Scheme 35.
Scheme 35.
Cu-catalyzed aminoarylation of cyclopropenes with organoboron reagents and O-benzoylhydroxylamines.
Scheme 36.
Scheme 36.
Photoredox and Ni-catalyzed three-component aminoarylation of electron-rich alkenes.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Zeng X, Chem. Rev 2013, 113, 6864–6900. - PubMed
    1. Njardarson Group. Top Pharmaceuticals Poster. njardarson.lab.arizona.edu/content/top-pharmaceuticals-poster (accessed 2020)
    1. Wu Z, Hu M, Li J, Wu W, Jiang H, Org. Biomol. Chem 2021, 19, 3036–3054; - PubMed
    2. Chen X, Xiao F, He W-M, Org. Chem. Front 2021, 8, 5206–5228;
    3. Kaur N, Wu F, Alom N-E, Ariyarathna JP, Saluga SJ, Li W, Org. Biomol. Chem 2019, 17, 1643–1654. - PubMed
    1. Freeman S, Alder JF, Eur. J. Med. Chem 2002, 37, 527–539; - PubMed
    2. Dalley JW, Everitt BJ, Semin. Cell Dev. Biol 2009, 20, 403–410. - PubMed
    1. Aube J, Peng X, Wang Y, Takusagawa F, J. Am. Chem. Soc 1992, 114, 5466–5467.

LinkOut - more resources