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  Dicationic phosphonium salts: Lewis acid initiators for the Mukaiyama-aldol reaction

Barrado, A. G., Bayne, J. M., Johnstone, T. C., Lehmann, C. W., Stephan, D. W., & Alcarazo, M. (2017). Dicationic phosphonium salts: Lewis acid initiators for the Mukaiyama-aldol reaction. Dalton Transactions, 46(46), 16216-16227. doi: 10.1039/C7DT03197A.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0000-FC6F-9 Version Permalink: http://hdl.handle.net/21.11116/0000-0000-FC70-6
Genre: Journal Article

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 Creators:
Barrado, Alejandro G.1, Author
Bayne, Julia M.2, Author
Johnstone, Timothy C.2, Author
Lehmann, Christian W.3, Author              
Stephan, Douglas W.2, Author
Alcarazo, Manuel1, Author
Affiliations:
1Institut für Organische und Biomelekulare Chemie, Georg-August-Universität Göttingen, Tammannstraβe 2, 37077 Göttingen, Germany , ou_persistent22              
2Department of Chemistry, University of Toronto, 80 St. George St, Toronto, Canada , ou_persistent22              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: Two strategies were used to prepare dicationic phosphonium cations. The first method consists of the reaction of 1-chlorocyclopropenium salts with phosphines to obtain cyclopropenium-substituted phosphonium salts 10a–f[BF4]. Anion exchange was performed to access the corresponding [B(C6F5)4] analogues 10a–f[B(C6F5)4], which showed much higher solubility in organic solvents. In addition, we developed a synthesis of dicationic phosphonium salts containing 2-, 3-, or 4-methylpyridinium substituents 11a–c[TfO], which were converted as well to their [B(C6F5)4] analogues 11a–c[B(C6F5)4]. Finally, the phenoxy-substituted phosphonium salt 12[B(C6F5)4] was also prepared. All salts demonstrated remarkable stability in air as compared with their fluorinated analogues. The Lewis acidity of these salts was evaluated by means of theoretical calculations and finally, they were shown to be effective in initiating the Mukaiyama-aldol reaction.

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Language(s): eng - English
 Dates: 2017-08-292017-11-022017-11-142017-12-14
 Publication Status: Published in print
 Pages: 12
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1039/C7DT03197A
 Degree: -

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Title: Dalton Transactions
  Abbreviation : Dalton Trans.
Source Genre: Journal
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Publ. Info: Cambridge, UK : Royal Society of Chemistry
Pages: - Volume / Issue: 46 (46) Sequence Number: - Start / End Page: 16216 - 16227 Identifier: ISSN: 1477-9226
CoNE: /journals/resource/954925269323