Global Access to 3/4-Phosphorylated Heterocycles via a Carbene-Catalyzed Stetter Reaction of Vinylphosphonates and Aldehydes

The first global method for the preparation of 3-phosphorylated-pyrroles, -furans, -thiophenes, and 4-phosphorylated 2,5-dihydropyridazines is reported. To achieve this, the first protocol for the direct synthesis of alpha-phosphorylated 1,4-diketones has been developed through a carbene-catalyzed S...

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Published inJournal of organic chemistry Vol. 85; no. 12; pp. 8166 - 8175
Main Authors Verma, Ram Subhawan, Mishra, Monika, Pandey, Chandra Bhan, Kumar, Shailesh, Tiwari, Bhoopendra
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.06.2020
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The first global method for the preparation of 3-phosphorylated-pyrroles, -furans, -thiophenes, and 4-phosphorylated 2,5-dihydropyridazines is reported. To achieve this, the first protocol for the direct synthesis of alpha-phosphorylated 1,4-diketones has been developed through a carbene-catalyzed Stetter reaction of vinylphosphonates and aldehydes. This is the first synthetic method for accessing 4-phosphorylated 2,5-dihydropyridazines. This process is metal-free and produces multifunctionalized heterocycles.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c00150