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Title
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Visible-light-induced [3+2] cycloadditions of donor/donor diazo intermediates with alkenes to achieve (spiro)-pyrazolines and pyrazoles
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Author
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Abstract
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| To date, [3 + 2] cycloadditions of diazo esters with alkynes or alkenes have been a robust tool to generate pyrazoles and pyrazolines. However, methods capable of generating donor/donor diazo species from readily available N-tosylhydrazones to furnish [3 + 2] cycloadditions, remain elusive. Herein, we describe the first visible-light-induced [3 + 2] cycloadditions of donor/donor diazo precursors with alkenes to afford pyrazoles and novel (spiro)pyrazolines bearing a quaternary center. This protocol shows a tolerable substrate scope covering versatile carbonyl compounds and alkenes. Late-stage functionalization of bioactive molecules, one-pot approach, and gram-scale synthesis have also been introduced successfully to prove the practicability. At last, mechanistic experiments and DFT studies suggested the formation of non-covalent interactions enabling the activation of N-tosylhydrazones and the formation of the donor/donor diazo intermediates. Visible-light-induced [3+2] cycloadditions of donor/donor diazo precursors with alkenes to afford pyrazoles and (spiro)pyrazolines have been reported. Mechanistic and DFT studies suggested the non-covalent interactions promote the reaction. |
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Language
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English
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Source (journal)
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Chemical science. - Cambridge, 2010, currens
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Publication
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Cambridge
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Royal Society of Chemistry
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2023
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ISSN
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2041-6520
[print]
2041-6539
[online]
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DOI
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10.1039/D3SC04188C
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Volume/pages
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14
:38
(2023)
, p. 10411-10419
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ISI
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001066613500001
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Pubmed ID
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37799991
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Full text (Publisher's DOI)
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Full text (open access)
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