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DOI: 10.1055/a-2353-1722
Magnesium-Mediated Regioselective Additions of Bromoform to Quinone Methides and Aurone-Derived Azadienes
I.N.N.N. thanks Science and Engineering Research Board (SERB), India for funding. D. K. Thanks CSIR India and N. S. thanks UGC India for a research fellowship.
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Abstract
The magnesium-mediated addition of bromoform to conjugated electron-deficient alkenes and imines, such as para-quinone methides (p-QMs) and aurone-derived azadienes, respectively, is reported here for the first time. While p-QMs undergo exclusive and hitherto unreported 1,6-addition of bromoform to afford benzylic tribromomethylated diarylmethanes, aurone-derived azadienes undergo both 1,2- and 1,4-additions to furnish α- and γ-tribromomethylamines. A mechanism involving the intermediacy of the tribromomethyl radical has been proposed based on control experiments and EPR studies. Representative synthetic transformations have also been carried out.
Key words
magnesium-mediated addition - bromoform - conjugate addition - p-quinone methides - azadienes - diarylmethanesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2353-1722.
- Supporting Information
Publikationsverlauf
Eingereicht: 21. Mai 2024
Angenommen nach Revision: 26. Juni 2024
Accepted Manuscript online:
26. Juni 2024
Artikel online veröffentlicht:
25. Juli 2024
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