Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 14, Pages 3792-3796Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800389
Keywords
cyclization; indolines; iodonium ylides; Nheterocycles; tertiary aryl amines
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Funding
- Fundamental Research Fund of Shandong University [2017JC004]
- National Natural Science Foundation of China [21772113, 21302075, 11501454]
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Described herein is a direct cyclization of simple tertiary aryl amines with iodonium ylides leading to a broad range of N-heterocycles. Completely different from the known reactivity of iodonium ylides, the finding reported herein is that an iodonium ylide is capable of cleaving a C(sp(3))-H bond and accepting two hydrogen atoms of a tertiary aryl amine, thus inducing a novel cyclization process. This transformation can proceed without the assistance of a transition-metal catalyst and eliminates the need for the premodification of the amine or the use of an additional initiator/oxidant.
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