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
. 2010 Jun 4;12(11):2450-2.
doi: 10.1021/ol1001686.

Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride

Chan Pil Park  1 , Joo Ho Lee, Kyung Soo Yoo, Kyung Woon Jung
Affiliations

Efficient diacetoxylation of alkenes via Pd(II)/Pd(IV) process with peracetic acid and acetic anhydride

Chan Pil Park et al. Org Lett. .

Abstract

A palladium-catalyzed diacetoxylation of alkenes in the presence of peracetic acid and acetic anhydride was developed to produce diacetates efficiently and diastereoselectively. Due to its mild conditions, this method was suitable for a broad range of substrates encompassing conjugated and nonconjugated olefins.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Plausible Pd(II)/Pd(IV) pathway.
Scheme 1
Scheme 1
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Chevrin C, Le Bras J, Henin F, Muzart J. Synthesis. 2005:2615–28618.
    2. Schultz MJ, Sigman MS. J. Am. Chem. Soc. 2006;128:1460–1463. - PubMed
    3. Thiery E, Chevrin C, Le Bras J, Harakat D, Muzart J. J. Org. Chem. 2007;72:1859–1862. - PubMed
    4. Zhang Y, Sigman MS. J. Am. Chem. Soc. 2007;129:3076–3077. - PubMed
    5. Jensen KH, Sigman MS. Org. Biomol. Chem. 2008;6:4083–4088. - PMC - PubMed
    1. Finn MG, Sharpless KB. J. Am. Chem. Soc. 1991;113:113–126.
    2. Crispino GA, Ho PT, Sharpless KB. Science. 1993;259:64–66. - PubMed
    3. Kolb HC, VanNieuwenhze MS, Sharpless KB. Chem. Rev. 1994;94:2483–2547.
    4. Kobayashi S, Endo M, Nagayama S. J. Am. Chem. Soc. 1999;121:11229–11230.
    5. Donohoe TJ, Blades K, Winter JJG, Stemp G. Tetrahedron Lett. 2000;41:4701–4704.
    6. Donohoe TJ. Synlett. 2002;8:1223–1232.
    7. Donohoe TJ, Harris RM, Butterworth S, Burrows JN, Cowley A, Parker JS. J. Org. Chem. 2006;71:4481–4489. - PubMed
    8. Christie SDR, Warrington AD. Synthesis. 2008:1325–1341.
    1. Li Y, Song D, Dong VM. J. Am. Chem. Soc. 2008;130:2962–2964. - PubMed
    2. Wang A, Jiang H, Chen H. J. Am. Chem. Soc. 2009;131:3846–3847. - PubMed
    1. Dick AR, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004;126:2300–2301. - PubMed
    2. Desai LV, Sanford MS. Angew. Chem. Int. Ed. 2007;46:5737–5740. - PubMed
    1. Nagata R, Saito I. Synlett. 1990:291–301.
    2. Chen MJY, Kochi JK. J. Chem. Soc., Chem. Commun. 1977:204–205.
    3. Muzart J. J. Mol. Cat. A: Chemical. 2007;276:62–72.

Publication types