Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 10, Pages 1919-1925Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701551
Keywords
Amination; 2-alkenylaniline; hypervalent iodine compound; indole; C-N bond formation
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Funding
- Overseas 100 Talents Program of Guangxi Higher Education, Basic Research Program of Guangxi Normal University [2014ZD005]
- National Natural Science Foundation of China [21562005, 21602037, 21462008]
- Natural Science Foundation of Guangxi [2016GXNSFFA380005]
- State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China [CMEMR2015-A05]
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A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline.
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