Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 12, Pages 6417-6425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00620
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Funding
- Overseas 100 Talents Program of Guangxi Higher Education
- National Natural Science Foundation of China [21562005, 21602037, 21462008]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China [CMEMR2015-A05, CMEMR2014-A01]
- Ministry of Education of China [IRT_16R15]
- Natural Science Foundation of Guangxi [2015GXNSFCA139001, 2016GXNSFFA380005]
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A copper-catalyzed selective cross-coupling reaction of 3-(hydroxyimino)indolin-2-ones with alkenyl boronic acids to access (E)-N-vinyl oxindole nitrones has been achieved under mild conditions. The studies showed that catalytic copper salt selectively to gave mono N-vinylation products, while 2.0 equiv of copper salt 8 examples yields provided double N-vinylation products. The control experiments revealed that the carbonyl group in 3-(hydroxyimino)indolin-2-one played important roles on N-vinylation. Furthermore, the prepared N-vinyl oxindole nitrones could be converted to spirooxindoles in good yields under thermal conditions.
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