Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 18, Pages 5151-5155Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801894
Keywords
C-H activation; cyclizations; dearomatization; heterocycles; palladium
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Funding
- Key Science and Technology Innovation Team of Shaanxi Province [2017KCT-37]
- National Science Foundation of China [21672169]
- Northwest University [YYB17007]
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Reported is a highly chemoselective intermolecular annulation of indole-based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani-type C-H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp(2))-C(sp(3)) and one C(sp(2))-C(sp(2)) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment, in good yields with excellent functional-group tolerance. Preliminary mechanistic studies reveal that C-H bond cleavage is likely involved in the rate-determining step, and the indole dearomatization might take place through an olefin coordination/insertion and -hydride elimination Heck-type pathway.
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