Display options
Cite
Barham JP, John MP, Murphy JA. One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein J Org Chem. 2014;10:2981-8doi: 10.3762/bjoc.10.316.
Barham, J. P., John, M. P., & Murphy, J. A. (2014). One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein journal of organic chemistry, 102981-8. https://doi.org/10.3762/bjoc.10.316
Barham, Joshua P, et al. "One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates." Beilstein journal of organic chemistry vol. 10 (2014): 2981-8. doi: https://doi.org/10.3762/bjoc.10.316
Barham JP, John MP, Murphy JA. One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014. PMID: 25550765; PMCID: PMC4273301.
Copy Download .nbib Format: NLM
Share it on

Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014.

One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates.

Beilstein journal of organic chemistry

Joshua P Barham, Matthew P John, John A Murphy

Affiliations

  1. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom ; GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom.
  2. GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom.
  3. WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

PMID: 25550765 PMCID: PMC4273301 DOI: 10.3762/bjoc.10.316

Abstract

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible light-assisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.

Keywords: iminium salt; organometallic; oxidative functionalisation; photoredox catalysis; tetrahydroisoquinoline

References

  1. Chem Rev. 2013 Jul 10;113(7):5322-63 - PubMed
  2. Org Lett. 2012 Feb 3;14(3):672-5 - PubMed
  3. J Am Chem Soc. 2005 May 18;127(19):6968-9 - PubMed
  4. Arch Pharm (Weinheim). 1996 Jan;329(1):11-22 - PubMed
  5. J Am Chem Soc. 2012 Mar 21;134(11):5317-25 - PubMed
  6. Am J Med Sci. 1963 Nov;246:550-7 - PubMed
  7. Org Lett. 2011 Aug 5;13(15):3852-5 - PubMed
  8. J Phys Chem B. 2011 Feb 3;115(4):678-84 - PubMed
  9. Chem Rev. 2002 May;102(5):1669-730 - PubMed
  10. Org Lett. 2013 Dec 6;15(23):5928-31 - PubMed
  11. Angew Chem Int Ed Engl. 2012 Aug 20;51(34):8656-60 - PubMed
  12. Org Lett. 2013 Jul 19;15(14):3650-3 - PubMed
  13. Chem Soc Rev. 2012 Dec 7;41(23):7687-97 - PubMed
  14. Neurotox Res. 2014 Jan;25(1):1-12 - PubMed
  15. Chem Commun (Camb). 2012 Feb 25;48(17):2337-9 - PubMed
  16. Chem Rev. 2013 Jan 9;113(1):271-401 - PubMed
  17. Org Lett. 2013 Mar 1;15(5):1092-5 - PubMed
  18. J Am Chem Soc. 2002 Jul 10;124(27):7894-5 - PubMed
  19. Chem Sci. 2014 Nov;5(11):4173-4178 - PubMed
  20. J Org Chem. 2012 Feb 17;77(4):1617-22 - PubMed
  21. Org Lett. 2013 Feb 1;15(3):574-7 - PubMed
  22. Org Biomol Chem. 2014 Apr 14;12(14):2189-92 - PubMed
  23. Beilstein J Org Chem. 2013 Oct 01;9:1977-2001 - PubMed
  24. Org Lett. 2012 Jan 6;14(1):94-7 - PubMed
  25. Org Lett. 2008 Sep 4;10(17):3661-3 - PubMed
  26. J Org Chem. 2013 Apr 19;78(8):4107-14 - PubMed
  27. Org Lett. 2004 Dec 23;6(26):4997-9 - PubMed
  28. Org Lett. 2008 Jun 19;10(12):2441-4 - PubMed
  29. Chem Sci. 2014 Jan;5(1):null - PubMed
  30. J Med Chem. 2005 Oct 20;48(21):6597-606 - PubMed
  31. J Org Chem. 2010 Jun 4;75(11):3916-9 - PubMed
  32. J Am Chem Soc. 2010 Feb 10;132(5):1464-5 - PubMed
  33. J Med Chem. 1990 Jan;33(1):147-52 - PubMed
  34. Chemistry. 2012 Apr 23;18(17):5170-4 - PubMed
  35. Chem Soc Rev. 2013 Jan 7;42(1):97-113 - PubMed

Publication Types