Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 9, Pages 5643-5659Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c03118
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Funding
- National Natural Science Foundation of China [22078084, 51874132]
- Scientific Research Fund of Hunan Provincial Education Department [20A224, 21A0407]
- Science and Technology Planning Project of Hunan Province [2020RC3056, 2018TP1017]
- Natural Science Foundation of Hunan Province [2020JJ5221, 2020JJ5212]
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A method for the preparation of 3-alkylated spiro[4.5]trienones via alkylation/ipso-cyclization reaction of activated alkynes with 4-alkyl-DHPs under transition-metal-free conditions is proposed. The mechanism studies indicate that the alkylation/ipso-cyclization reaction involves radical processes. This ipso-cyclization procedure offers a series of advantages, including accessibility, mild conditions, high efficiency, greater safety, and environmental friendliness.
A method for the preparation of 3-alkylated spiro[4.5]trienonesviaalkylation/ipso-cyclization of activated alkyneswith 4-alkyl-DHPs under transition-metal-free conditions is proposed. This alkylation successively undergoes the generation of alkylradicals, addition of alkyl radicals to the alkynes, and intramolecular ipso-cyclization. The mechanism studies suggest that thealkylation/ipso-cyclization involves a radical process. This ipso-cyclization procedure shows a series of advantages, such asaccessibility, mild conditions, high efficiency, greater safety, and an environmentally friendly method
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