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

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

The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising...

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Bibliographic Details
Main Authors: Soundararajan Karthikeyan, Radha Krishnan Shobana, Kamarajapurathu Raju Subimol, J. Helen Ratna Monica, Ayyanoth Karthik Krishna Kumar
Format: Article
Language:English
Published: Beilstein-Institut 2020-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
halomethylcoumarin
morita–baylis–hillman adducts
organocatalyst
phosphonium salt
triazolation
Online Access:https://doi.org/10.3762/bjoc.16.130
Description
Summary:The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.
ISSN:1860-5397

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