Azidophosphonium salt directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromo-methyl coumarins from Baylis-Hillman adducts

  1. S Karthikeyan,
  2. R Shobana,
  3. K R Subimol,
  4. J Helen Ratna Monica and
  5. Ayyanoth Karthik Krishna KumarORCID Logo

Submitting author affiliation: The American College, Madurai, India

Beilstein Arch. 2020, 202038. https://doi.org/10.3762/bxiv.2020.38.v1

Published 01 Apr 2020

  • Preprint

Abstract

Direct transformation of Baylis Hillman adducts into molecules of interest is a crucial process, thereby allylic hydroxy protected or halogenated BH adducts are commonly preferred.  Herein, we report a azidophosphonium salt catalysed (QPS) straight forward protcol for synthesising structurally demanding (E) / (Z) cinnamyl-1H-1,2,3-triazoles and halomethyl coumarins from unaltered BH adducts.  Novel methodology, efficient catalyst and direct utilization of BH adducts in presence mild reaction conditions identifies the reported procedures as a powerful synthetic tool.

Keywords: Phosphonium salt, Baylis-Hillman adducts, Halomethyl coumarin, Triazolation, Organocatalyst

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Karthikeyan, S.; Shobana, R.; Subimol, K. R.; Ratna Monica, J. H.; Krishna Kumar, A. K. Beilstein Arch. 2020, 202038. doi:10.3762/bxiv.2020.38.v1

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