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
. 2021 Mar 12;27(15):4883-4887.
doi: 10.1002/chem.202005449. Epub 2021 Feb 15.

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C-S Formation

Nate W J Ang  1 , Lutz Ackermann  1   2
Affiliations

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C-S Formation

Nate W J Ang et al. Chemistry. .

Abstract

Sulfur-containing molecules are of utmost topical importance towards the effective development of pharmaceuticals and functional materials. Herein, we present an efficient and mild electrochemical thiolation by cross-electrophile coupling of alkyl bromides with functionalized bench-stable thiosulfonates to access alkyl sulfides with excellent efficacy and broad functional group tolerance. Cyclic voltammetry and potentiostatic analysis were performed to elucidate mechanistic insights into this electrocatalytic thiolation reaction.

Keywords: cross-electrophile coupling; electrosynthesis; nickel; reductive; thiolation.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Electrochemical nickel‐catalyzed cross‐electrophile thiolation.
Scheme 2
Scheme 2
Nickel‐catalyzed electro‐reductive thiolation of alkylbromide 1 a with substituted thiosulfonates 2. Faradaic yield given in parentheses.
Scheme 3
Scheme 3
Nickel‐catalyzed electro‐reductive thiolation with bromides 1. Faradaic yield given in parentheses.
Figure 1
Figure 1
Cyclic voltammetry (DMF, 0.1 m nBu4NPF6, 100 mVs−1) with glassy carbon as the working electrode. Cyclic voltammograms of different reaction components.
Scheme 4
Scheme 4
Potentiostatic studies.
Scheme 5
Scheme 5
Plausible catalytic cycle.
See this image and copyright information in PMC

References

    1. None
    1. Wang J.-M., Ding G.-Z., Fang L., Dai J.-G., Yu S.-S., Wang Y.-H., Chen X.-G., Ma S.-G., Qu J., Xu S., Du D., J. Nat. Prod. 2010, 73, 1240–1249; - PubMed
    1. Guo H., Sun B., Gao H., Chen X., Liu S., Yao X., Liu X., Che Y., J. Nat. Prod. 2009, 72, 2115–2119; - PubMed
    1. Thase M. E., Macfadden W., Weisler R. H., Chang W., Paulsson B., Khan A., Calabrese J. R., J. Clin. Psychopharmacol. 2006, 26, 600–609; - PubMed
    1. Piscitelli S. C., Goss T. F., Wilton J. H., D′Andrea D. T., Goldstein H., Schentag J. J., Antimicrob. Agents Chemother. 1991, 35, 1765–1771; - PMC - PubMed

Grants and funding

LinkOut - more resources