Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 10, Pages 2311-2316Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500317
Keywords
cations; C-N bond formation; C-O bond formation; fused-ring systems; heterocycles; photocatalysis
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Funding
- University of Arkansas, Arkansas Bioscience Institute from the National Institute of General Medical Sciences of the National Institutes of Health (NIH) [P30 GM103450]
- NSF Career Award [CHE-1255539]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1255539] Funding Source: National Science Foundation
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The synthesis of fused N-arylindolines using visible light photoredox catalysis has been developed. We previously described that photogenerated amine radical cations generate substituted indoles through an intermediate benzylic carbocation. Herein, we expand the application of this chemistry by trapping the benzylic carbocation with tethered heteronucleophiles. The reactivity of the photogenerated benzylic carbocation is explored and applied to a range of substrates with various electronic characters and ring constraints. The method described provides C-2 and C-3 fused indolines bearing a tetrasubstituted carbon stereocenter with greater than 99:1 diastereoselectivity in moderate to good yields.
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