Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 51, Pages 18730-18738Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503732
Keywords
heterocycles; metallacycles; multicomponent reactions; synthetic methods; titanium
Categories
Funding
- Landesgraduiertenforderung (LGF Funding Program of the state of Baden-Wurttemberg)
- University of Heidelberg
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Consecutive C- and N-arylation of N-heterocyclic nitriles is mediated by titanium(IV) alkoxides. The carbo-and azaphilic arylation step may be separated by choosing the order in which the two equivalents of aryl transfer reagent are added. In the course of this transformation, the ancillary N-heterocycle acts as both a directing anchor group and electron reservoir. In the selectivity-determining step, the selectivity is governed by a choice between (direct) C- and Ti-arylation; the latter opens up a reaction pathway that allows further migration to the nitrogen atom. The isolation of metal-containing aggregates from the reaction mixture and computational studies gave insights into the reaction mechanism. Subsequently, a multicomponent one-pot protocol was devised to rapidly access complex quaternary carbon centers.
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