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
. 2023 Aug;55(15):2353-2360.
doi: 10.1055/s-0041-1738430. Epub 2022 Dec 20.

Synthesis of N-Acylsulfenamides from Amides and N-Thiosuccinimides

Jessica T Liu  1 , Daniel S Brandes  1 , Nathaniel S Greenwood  1 , Jonathan A Ellman  1
Affiliations

Synthesis of N-Acylsulfenamides from Amides and N-Thiosuccinimides

Jessica T Liu et al. Synthesis (Stuttg). 2023 Aug.

Abstract

Herein is reported a robust and general method for the preparation of N-acylsulfenamides, important functionalities that have recently been utilized as central inputs for the asymmetric synthesis of high oxidation state sulfur compounds. This straightforward transformation proceeds by reaction of primary amides, carbamates, sulfonamides, sulfinamides, and ureas with stable N-thiosuccinimides or N-thiophthalimides, which in turn are prepared in a single step from commercial thiols. The use of stable N-thiosuccinimide and N-thiophthalimide reactants is desirable because it obviates the use of highly reactive sulfenyl chlorides.

Keywords: amide; asymmetric catalysis; sulfenamide; thiol; thiophthalimide; thiosuccinimide.

PubMed Disclaimer

Conflict of interest statement

Conflict of Interest The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Background on the synthesis and application of N-acylsulfenamides
Scheme 2
Scheme 2
Scope of amide input
Scheme 3
Scheme 3
Scope of thiosuccinimide input
See this image and copyright information in PMC

References

    1. Craine L; Raban M Chem. Rev 1989, 89, 689.
    2. Koval IV Russ. Chem. Rev 1996, 65, 421.
    3. Cao Y; Abdolmohammadi S; Ahmadi R; Issakhov A; Ebadi AG; Vessally E RSC Adv. 2021, 11, 32394. - PMC - PubMed
    1. Greenwood NS; Champlin AT; Ellman JA J. Am. Chem. Soc 2022, 144, 17808. - PMC - PubMed
    1. Ma L; Bai L; Yu Z; Shen Q Chirality 2022, 34, 1191. - PubMed
    1. Behforouz M; Kerwood JE J. Org. Chem 1969, 34, 51.
    2. Harpp DN; Mullins DF; Steliou K; Triassi IJ Org. Chem 1979, 44, 4196.
    3. Koval IV; Tarasenko AI; Kremlev MM; Molchanova NR Zh. Org. Khim 1981, 17, 533.
    4. Miura Y; Shibata Y; Kinoshita M Bull. Chem. Soc. Jpn 1986, 59, 3291.
    5. Perrio S; Reboul V; Metzner P In Science of Synthesis., Vol. 31a; Ramsden CA, Ed.; Georg Thieme Verlag: Stuttgart, 2007, 1041.
    6. Ma L-J; Chen S-S; Li G-X; Zhu J; Wang Q-W; Tang Z ACS Catal. 2019, 9, 1525.
    1. Chen Q; Shen M; Tang Y; Li C Org. Lett 2005, 7, 1625. - PubMed
    2. Zhang X-S; Zhang X-H Phosphorus, Sulfur Silicon Relat. Elem 2016, 191, 89. - PMC - PubMed

LinkOut - more resources