[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the CpLigand

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A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium-catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp-bound rhodium species.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2017-02
Language
English
Article Type
Article
Keywords

C-H ACTIVATION; N BOND FORMATION; CYCLOPENTADIENYL LIGANDS; AMBIENT CONDITIONS; FACILE SYNTHESIS; DIAZO-COMPOUNDS; DIRECTING GROUP; OXIME ESTERS; ALKENES; FUNCTIONALIZATION

Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.56, no.9, pp.2408 - 2412

ISSN
1433-7851
DOI
10.1002/anie.201612559
URI
http://hdl.handle.net/10203/223026
Appears in Collection
CH-Journal Papers(저널논문)
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