Journal
ORGANIC LETTERS
Volume 22, Issue 19, Pages 7577-7580Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02781
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Funding
- JSPS [16K17901]
- Grants-in-Aid for Scientific Research [16K17901] Funding Source: KAKEN
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Copper-mediated [3 + 2] annulation of alkenes with anitrobenzyl bromides has been developed. The reaction is promoted simply by a copper salt to produce the corresponding 2-isoxazoline N-oxides with perfect regioselectivity. The present method can be conducted under mild conditions, affording a diverse array of 2-isoxazoline N-oxides. The obtained products can readily be converted to the related heterocycles such as 2-isoxazoline and isoxazole. A radical-polar crossover pathway initiated by single-electron transfer from nitronate to a copper salt is proposed.
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