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Facile NBS/DMSO mediated dibromination of olefins including selected natural products and glycals

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Abstract

A highly chemo- and diastereoselective vic-dibromination of olefins has been developed. The process employs a readily available N-Bromosuccinimide (NBS)/DMSO reagent system as a bromine source. High substrate scope, simple reaction conditions, application to natural products and glycals makes the process very attractive.

Graphical abstract

A highly chemo- and diastereoselective vic-dibromination of olefins has been developed. The process employs a readily available N-Bromosuccinimide (NBS)/DMSO reagent system as a bromine source. High substrate scope, simple reaction conditions, application to natural products and glycals makes the process very attractive.

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References

  1. Megha K and Jakob M 2015 Bromination of Olefins with HBr and DMSO J. Org. Chem. 80 3701

    Article  Google Scholar 

  2. (a) Kutsumura N, Kubokawa K and Saito T 2011 Synthesis 2377; (b) Ranu B C and Jana R 2005 Catalysis by Ionic Liquid. A Green Protocol for the Stereoselective Debromination of vicinal-Dibromides by [pmIm]BF4 under Microwave Irradiation J. Org. Chem. 70 8621; (c) Ranu B C, Das A and Hajira A 2003 Dichloroindium Hydride(Cl2InH): A Convenient Reagent for Stereoselective Reduction of vic-Dibromides to (E)-Alkenes Synthesis 1012

  3. (a) Goudreau N, Brochu. C, Cameron D R, Duceppe J S, Faucher A M, Ferland J M, Grand-Maître C, Poirier M, Simoneau B and Tsantrizos Y S 2004 Potent inhibitors of the hepatitis C virus NS3 protease: design and synthesis of macrocyclic substrate-based beta-strand mimics J. Org. Chem. 69 6185; (b) Arrault A, Guillaumet G, Leger J M, Jarry C and Merour J Y 2002 A Straightforward Synthesis of Oxazino[2,3,4-ij]quinoline Derivatives from 8-Hydroxyquinolines Synthesis 1879

  4. Kutsumura N, Kiriseko A and Saito T 2012 First total synthesis of (+)-heteroplexisolide E Tetrahedron Lett. 53 3274

  5. (a) Primerano P, Cordaro M and Scala A 2013 Direct sustainable bromination of alkenes in aqueous media and basic ionic liquids Tetrahedron Lett. 54 4061 and references cited therein; (b) Smith M B 2013 In March's Advanced Organic Chemistry 7th edn. (Wiley) p. 982 and references therein

  6. Yu T-Y, Wang Y, Hu X-Q and Xu P-F 2014 Triphenylphosphine oxide-catalyzed stereoselective poly- and dibromination of unsaturated compounds Chem. Commun. 50 7817 and references therein

  7. Reddi R N, Prasad P K and Sudalai A 2014 I2-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives Org. Lett. 16 5674; (b) Prasad P K, Reddi R N and Sudalai A 2016 Regioselective Oxo-Amination of Alkenes and Enol Ethers with N-Bromosuccinimide-Dimethyl Sulfoxide Combination: A Facile Synthesis of α-Amino-Ketones and Esters Org. Lett. 18 500

  8. Ramos A, Rivero R, Visozo A, Piloto J and García A 2002 Parthenin, a sesquiterpene lactone of Parthenium hysterophorus L. is a high toxicity clastogen Mutat. Res. 15 19

  9. Chou S Y, Hsu C S, Wang K T, Wang M C and Wang C C 2007 Antitumor effects of Osthol from Cnidium monnieri: an in vitro and in vivo study Phytother. Res. 21 226

    Article  CAS  Google Scholar 

  10. Marija C, Mirjana V, Dejan S, Dragan M, Neso S, Laszlo S and Rastko V D 2008 Electrochemical Bromination of Peracetylated Glycals Adv. Synth. Catal. 350 29 and references cited therein

  11. Paul B and Descostes G 1976 Additions comparées des halogenès sur le 3,4,6-tri-O-acétyl-1,5-anhydro-1,5-didésoxy-, d-arabino-hex-1-énitol et l'analogue 3,4,6-tri-O-benzylé; effets de solvant sur la formation spécifique des dérivés 1,2-didésoxy-1,2-dihalogéno-α-d-glucopyranoses Carb. Res. 51 55; (b) Marcus T, Gerard D and Dominique L 1993 Bromination of 1,5-Anhydrohex-1-enitols (Glycals) Using Quaternary Ammonium Tribromides as Bromine Donors: Synthesis of α-1,2-trans-2-Bromo-2-deoxyglycopyranosyl Bromides and Fluorides Synthesis 889

  12. Boschi A, Chiappe C, Rubertis A D and Ruasse M F 2000 Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals and related cyclic enol ethers J. Org. Chem. 65 8470

    Article  CAS  Google Scholar 

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Acknowledgement

The authors are highly thankful to director CSIR-IIIM (Indian Institute of Integrative Medicine) for the necessary facilities. SKY is highly obliged to DST-India for a research grant under the INSPIRE Faculty scheme. (IIIM-Publication number of the current study is IIIM/1828/2015).

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Correspondence to Syed Khalid Yousuf.

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Ul Lah, H., Mir, S.A., Hussain, G. et al. Facile NBS/DMSO mediated dibromination of olefins including selected natural products and glycals. J Chem Sci 134, 18 (2022). https://doi.org/10.1007/s12039-021-02003-3

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  • DOI: https://doi.org/10.1007/s12039-021-02003-3

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