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

DOI: 10.1021/acs.joc.0c00150

Source and publish data:

Journal of Organic Chemistry p. 8166 - 8175 (2020)

Update date:2022-08-03

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Authors:

Verma, Ram Subhawan

Mishra, Monika

Pandey, Chandra Bhan

Kumar, Shailesh

Tiwari, Bhoopendra

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Article abstract of DOI:10.1021/acs.joc.0c00150

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 α-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.

Full text of DOI:10.1021/acs.joc.0c00150

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