Display options
Cite
Chirila A, Gopal Das B, Paul ND, et al. Diastereoselective Radical-Type Cyclopropanation of Electron-Deficient Alkenes Mediated by the Highly Active Cobalt(II) Tetramethyltetraaza[14]annulene Catalyst. ChemCatChem. 2017;9(8):1413-1421doi: 10.1002/cctc.201601568.
Chirila, A., Gopal Das, B., Paul, N. D., & de Bruin, B. (2017). Diastereoselective Radical-Type Cyclopropanation of Electron-Deficient Alkenes Mediated by the Highly Active Cobalt(II) Tetramethyltetraaza[14]annulene Catalyst. ChemCatChem, 9(8), 1413-1421. https://doi.org/10.1002/cctc.201601568
Chirila, Andrei, et al. "Diastereoselective Radical-Type Cyclopropanation of Electron-Deficient Alkenes Mediated by the Highly Active Cobalt(II) Tetramethyltetraaza[14]annulene Catalyst." ChemCatChem vol. 9,8 (2017): 1413-1421. doi: https://doi.org/10.1002/cctc.201601568
Chirila A, Gopal Das B, Paul ND, de Bruin B. Diastereoselective Radical-Type Cyclopropanation of Electron-Deficient Alkenes Mediated by the Highly Active Cobalt(II) Tetramethyltetraaza[14]annulene Catalyst. ChemCatChem. 2017 Apr 21;9(8):1413-1421. doi: 10.1002/cctc.201601568. Epub 2017 Apr 24. PMID: 28529668; PMCID: PMC5413858.
Copy Download .nbib Format: NLM
Share it on

ChemCatChem. 2017 Apr 21;9(8):1413-1421. doi: 10.1002/cctc.201601568. Epub 2017 Apr 24.

Diastereoselective Radical-Type Cyclopropanation of Electron-Deficient Alkenes Mediated by the Highly Active Cobalt(II) Tetramethyltetraaza[14]annulene Catalyst.

ChemCatChem

Andrei Chirila, Braja Gopal Das, Nanda D Paul, Bas de Bruin

Affiliations

  1. Homogeneous, Supramolecular and Bio-Inspired Catalysis (HomKat)van't Hoff Institute for Molecular Sciences (HIMS) University of Amsterdam Science Park 9041098 XH Amsterdam The Netherlands.
  2. Present address: Department of Chemistry Indian Institute of Engineering Science and Technology Shibpur, Botanic Garden Howrah711 103 West Bengal India.

PMID: 28529668 PMCID: PMC5413858 DOI: 10.1002/cctc.201601568

Abstract

A new protocol for the catalytic synthesis of cyclopropanes using electron-deficient alkenes is presented, which is catalysed by a series of affordable, easy to synthesise and highly active substituted cobalt(II) tetraaza[14]annulenes. These catalysts are compatible with the use of sodium tosylhydrazone salts as precursors to diazo compounds in one-pot catalytic transformations to afford the desired cyclopropanes in almost quantitative yields. The reaction takes advantage of the metalloradical character of the Co complexes to activate the diazo compounds. The reaction is practical and fast, and proceeds from readily available starting materials. It does not require the slow addition of diazo reagents or tosylhydrazone salts or heating and tolerates many solvents, which include protic ones such as MeOH. The Co

Keywords: alkenes; cobalt; macrocyclic ligands; phase-transfer catalysis; reaction mechanisms

References

  1. Angew Chem Int Ed Engl. 2009;48(5):850-2 - PubMed
  2. Inorg Chem. 2013 Oct 7;52(19):11509-13 - PubMed
  3. J Am Chem Soc. 2016 Jul 20;138(28):8968-75 - PubMed
  4. Inorg Chem. 2015 Jan 5;54(1):273-9 - PubMed
  5. Inorg Chem. 2012 Mar 19;51(6):3352-4 - PubMed
  6. J Am Chem Soc. 2010 Aug 11;132(31):10891-902 - PubMed
  7. J Org Chem. 2003 Oct 17;68(21):8179-84 - PubMed
  8. J Am Chem Soc. 2007 Oct 10;129(40):12074-5 - PubMed
  9. J Org Chem. 2003 Nov 28;68(24):9433-40 - PubMed
  10. J Org Chem. 2007 Jan 19;72(2):650-3 - PubMed
  11. ChemCatChem. 2017 Apr 21;9(8):1413-1421 - PubMed
  12. Org Lett. 2015 Nov 6;17(21):5448-51 - PubMed
  13. J Am Chem Soc. 2001 May 9;123(18):4119-29 - PubMed
  14. Angew Chem Int Ed Engl. 2008;47(44):8460-3 - PubMed
  15. J Am Chem Soc. 2010 Sep 22;132(37):12796-9 - PubMed
  16. Inorg Chem. 2011 Oct 17;50(20):9896-903 - PubMed
  17. J Am Chem Soc. 2003 Sep 10;125(36):10926-40 - PubMed
  18. J Am Chem Soc. 2014 Apr 23;136(16):5856-9 - PubMed
  19. J Am Chem Soc. 2011 Jun 8;133(22):8518-21 - PubMed
  20. J Am Chem Soc. 2011 Mar 30;133(12):4330-41 - PubMed

Publication Types