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
. 2015 Feb 18;137(6):2195-8.
doi: 10.1021/ja512946e. Epub 2015 Feb 4.

Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling

David N Primer  1 , Idris Karakaya, John C Tellis, Gary A Molander
Affiliations

Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling

David N Primer et al. J Am Chem Soc. .

Abstract

Single-electron-mediated alkyl transfer affords a novel mechanism for transmetalation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyltrifluoroborates with an array of aryl bromides mediated by an Ir photoredox catalyst and a Ni cross-coupling catalyst.

PubMed Disclaimer

Figures

Figure 1
Figure 1
General catalytic cycle for secondary alkyl cross-coupling, depicting side reactions and off-cycle intermediates that may occur.
Figure 2
Figure 2
Comparison between traditional transmetalation and single-electron-mediated activation, and proposed catalytic cycle for photo-redox cross-coupling.
See this image and copyright information in PMC

References

    1. Roughley SD, Jordan AM. J. Med. Chem. 2011;54:3451. - PubMed
    1. Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011;111:1417. - PMC - PubMed
    1. Lozada J, Liu Z, Perrin DM. J. Org. Chem. 2014;79:5365. - PubMed
    1. Littke AF, Dai C, Fu GC. J. Am. Chem. Soc. 2000;122:4020.
    2. Dreher SD, Dormer PG, Sandrock DL, Molander GA. J. Am. Chem. Soc. 2008;130:9257. - PMC - PubMed
    3. van den Hoogenband A, Lange JHM, Terpstra JW, Koch M, Visser GM, Visser M, Korstanje TJ, Jastrzebski JTBH. Tetrahedron Lett. 2008;49:4122.
    4. Li L, Zhao S, Joshi-Pangu A, Diane M, Biscoe MR. J. Am. Chem. Soc. 2014;136:14027. - PMC - PubMed
    1. Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis. Sausalito, CA: University Science Books; 2009.

Publication types