Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 36, Issue 10, Pages 909-915Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201800301
Keywords
electrochemistry; indoline; radical; annulation; hinckdentine A
Categories
Funding
- MOST [2016YFA0204100]
- NSFC [21672178, 21603227]
- Fundamental Research Funds for the Central Universities
- Thousand Youth Talents Plan
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An electrochemical synthesis of functionalized (aza)indolines through dehydrogenative [3+2] annulation of arylamines with tethered alkenes has been developed. Previous reported syntheses through similar inter- and intramolecular annulation reactions required noble-metal catalysts and are mostly limited to terminal alkenes or 1,3-dienes. The electrosynthesis employs the easily available and inexpensive ferrocene as the molecular catalyst and is compatible with di-, tri- and even tetrasubstituted alkenes to construct indolines as well as the more challenging azaindolines. Employing the newly developed electrosynthesis as a key step, the total synthesis of marine alkaloid (+/-)-hinckdentine A has been achieved in 12 steps (longest linear sequence) from commercially available materials.
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