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  α-Dicationic Chelating Phosphines: Synthesis and Application to the Hydroarylation of Dienes

Gu, L., Wolf, L. M., Zieliński, A., Thiel, W., & Alcarazo, M. (2017). α-Dicationic Chelating Phosphines: Synthesis and Application to the Hydroarylation of Dienes. Journal of the American Chemical Society, 139(13), 4948-4953. doi:10.1021/jacs.7b01441.

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 Creators:
Gu, Lianghu1, Author              
Wolf, Lawrence M.2, 3, Author              
Zieliński, Adam4, Author
Thiel, Walter2, Author              
Alcarazo, Manuel4, Author
Affiliations:
1Research Group Alcarazo, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445592              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
3Department of Chemistry, University of Massachusetts Lowel, Lowell, Massachusetts 01854, United States, ou_persistent22              
4Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany, ou_persistent22              

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 Abstract: A series of new P^P-chelating ligands constituted by a dicationic −[P(H2Im)2]+2 unit (H2Im = 1,3-dimethyl-4,5-dihydroimidazol-2-ylidene) and a −PPh2 group connected through structurally different backbones have been synthesized. Evaluation of their reactivity toward different metal centers provides evidence that the dicationic fragment, otherwise reluctant to coordinate metals, readily participates in the formation of chelates when embedded into such a scaffold. Moreover, it significantly enhances the Lewis acidity of the metals to which it coordinates. This property has been used to develop a Rh catalyst that efficiently triggers the hydroarylation of dienes with electron-rich aromatic molecules. Kinetic studies and deuterium-labeling experiments, as well as density functional theory calculations, were performed in order to rationalize these findings.

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Language(s): eng - English
 Dates: 2017-02-102017-03-212017-04-05
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.7b01441
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 139 (13) Sequence Number: - Start / End Page: 4948 - 4953 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870