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Synthesis 2019; 51(15): 2945-2958
DOI: 10.1055/s-0037-1611577
DOI: 10.1055/s-0037-1611577
paper
DBU-Catalyzed Michael Reaction of Enones with 1,3-Diketones and the Subsequent Iodine-Mediated Transformation of the Adducts to Polysubstituted Phenols
We are grateful for the financial support from Natural Science Foundation of Jiangsu Province (BK20181462), the Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (BM2012110), and the Advanced Catalysis and Green Manufacturing Collaborative Innovation Center.Further Information
Publication History
Received: 12 February 2019
Accepted after revision: 24 March 2019
Publication Date:
18 April 2019 (online)
Abstract
An efficient DBU-catalyzed Michael reaction of enones with 1,3-diketones has been developed for the gram-scale preparation of the Michael adducts. It is attractive that most of the adducts can be obtained with high purity through simple filtration. A convenient I2-mediated transformation of the adducts to polysubstituted phenols has also been exploited. This conversion is remarkable with the cyclization and aromatization processes by using DBU as the base and I2 as the oxidant. Furthermore, hydroxylated (E)-stilbene derivatives can be easily prepared by using this method. The readily available starting materials, metal-free and mild conditions make this approach simple and practical.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611519.
- Supporting Information
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Although a similar condensation product as 36 was reported to transform to phenol in the presence of Br2, the acetyl group was unaffected in the product and no persuasive NMR data was provided, see: