Conversion of alkynes into 1,2-diketones using HFIP as sacrificial hydrogen donor and DMSO as dihydroxylating agent

[Display omitted] •HFIP as sacrificial hydrogen donor.•DMSO as dihydroxylating agent.•Conversion of internal alkynes into 1,2-diketones.•A metal-free and hypervalent iodine free phenomenon.•Broad substrate scope with high yields of the products. A metal-free and hypervalent iodine free conversion of...

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Veröffentlicht in:Tetrahedron letters 2020-03, Vol.61 (10), p.151588, Article 151588
Hauptverfasser: Gujjarappa, Raghuram, Vodnala, Nagaraju, Putta, V.P.R.K., Ganga Reddy, Velma, Malakar, Chandi C.
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Sprache:eng
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Zusammenfassung:[Display omitted] •HFIP as sacrificial hydrogen donor.•DMSO as dihydroxylating agent.•Conversion of internal alkynes into 1,2-diketones.•A metal-free and hypervalent iodine free phenomenon.•Broad substrate scope with high yields of the products. A metal-free and hypervalent iodine free conversion of internal alkynes into 1,2-diketo compounds has been described. The efficacy of the present protocol rely on the use of HFIP (1,1,1,3,3,3-Hexafluoro-2-propanol) as reducing agent of alkynes and DMSO as dihydroxylating agent of olefins to acquire the desired chemical transformations. The obtained 1,2-diketones were further transformed into useful derivatives.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151588