Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 5, Issue -, Pages -Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.5.1
Keywords
cyclization; electron transfer; indole; indoline; radical
Categories
Funding
- Overseas Research Scholarship (ORS)
- University of Strathclyde
- F. Hoffmann-La Roche, Ltd
- CASE award
- EPSRC
- EPSRC [EP/E036244/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/E036244/1] Funding Source: researchfish
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Tetrakis(dimethylamino) ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.
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