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Edmunds M, Raheem MA, Boutin R, et al. Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates. Beilstein J Org Chem. 2016;12:239-44doi: 10.3762/bjoc.12.25.
Edmunds, M., Raheem, M. A., Boutin, R., Tait, K., & Tam, W. (2016). Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates. Beilstein journal of organic chemistry, 12239-44. https://doi.org/10.3762/bjoc.12.25
Edmunds, Michael, et al. "Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates." Beilstein journal of organic chemistry vol. 12 (2016): 239-44. doi: https://doi.org/10.3762/bjoc.12.25
Edmunds M, Raheem MA, Boutin R, Tait K, Tam W. Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates. Beilstein J Org Chem. 2016 Feb 09;12:239-44. doi: 10.3762/bjoc.12.25. eCollection 2016. PMID: 26977182; PMCID: PMC4778517.
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Beilstein J Org Chem. 2016 Feb 09;12:239-44. doi: 10.3762/bjoc.12.25. eCollection 2016.

Regioselective palladium-catalyzed ring-opening reactions of C1-substituted oxabicyclo[2,2,1]hepta-2,5-diene-2,3-dicarboxylates.

Beilstein journal of organic chemistry

Michael Edmunds, Mohammed Abdul Raheem, Rebecca Boutin, Katrina Tait, William Tam

Affiliations

  1. Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada.

PMID: 26977182 PMCID: PMC4778517 DOI: 10.3762/bjoc.12.25

Abstract

Palladium-catalyzed ring-opening reactions of C1 substituted 7-oxanorbornadiene derivatives with aryl iodides were investigated. The optimal conditions for this reaction were found to be PdCl2(PPh3)2, ZnCl2, Et3N and Zn in THF. Both steric and electronic factors played a role in the outcome of the reaction as increasing the steric bulk on the bridgehead carbon decreased the yield. These reactions were found to be highly regioselective, giving only one of the two possible regioisomers in all cases. A diverse collection of novel, highly substituted biphenyl derivatives were obtained.

Keywords: aryl iodides; oxabenzonorbornadiene; palladium catalysis; regioselectivity; ring-opening reactions

References

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