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Phosphabicyclononane-Containing Ru Complexes: Efficient Pre-Catalysts for Olefin Metathesis Reactions

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Fabien Boeda,^† Hervé Clavier,^† Margaritha Jordaan,^‡ Wolfgang H. Meyer,^‡ and Steven P. Nolan*^†

Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, 43007 Tarragona, Spain, and Sasol Technology (Pty), Ltd., R&D Division, 1 Klasie Havenga Road, Sasolburg, 1947, South Africa

J. Org. Chem., 2008, 73 (1), pp 259–263

DOI: 10.1021/jo702169p

Publication Date (Web): December 6, 2007

Section:

General Organic Chemistry

Abstract

The catalytic performances of three Phosphabicyclononane (Phoban)-containing ruthenium-based pre-catalysts have been evaluated for metathesis transformations. A wide screening of substrates in ring-closing metathesis reactions reveals the greater efficiency of pre-catalyst 4. Comparison of the catalytic activities of 4 with Grubbs' first-generation pre-catalyst illustrates the key role of the Phoban ligand. Additionally, a comparative study of three Phoban-containing pre-catalysts has been conducted for the self-metathesis of 1-octene at low catalyst loading (25−100 ppm).

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Ruthenium-Based Olefin Metathesis Catalysts Derived from Alkynes
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Chemical Reviews2010 110 (8), 4865-4909
- Ruthenium-Based Olefin Metathesis Catalysts Derived from Alkynes
  Ana M. Lozano-Vila, Stijn Monsaert, Agata Bajek and Francis Verpoort
  Chemical Reviews2010 110 (8), 4865-4909
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Carbocyclic Carbene Metal Complexes
K. Öfele, E. Tosh, C. Taubmann and W. A. Herrmann
Chemical Reviews2009 109 (8), 3408-3444
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Anatomy of Phobanes. Diastereoselective Synthesis of the Three Isomers of n-Butylphobane and a Comparison of their Donor Properties
Monica Carreira, Manutsavin Charernsuk, Michael Eberhard, Natalie Fey, Roel van Ginkel, Alex Hamilton, Wilhelmus P. Mul, A. Guy Orpen, Hirihataya Phetmung and Paul G. Pringle
Journal of the American Chemical Society2009 131 (8), 3078-3092
- Anatomy of Phobanes. Diastereoselective Synthesis of the Three Isomers of n-Butylphobane and a Comparison of their Donor Properties
  Monica Carreira, Manutsavin Charernsuk, Michael Eberhard, Natalie Fey, Roel van Ginkel, Alex Hamilton, Wilhelmus P. Mul, A. Guy Orpen, Hirihataya Phetmung and Paul G. Pringle
  Journal of the American Chemical Society2009 131 (8), 3078-3092
  Three methods for the large scale (50−100 g) separation of the secondary phobanes 9-phosphabicyclo[3.3.1]nonane (s-PhobPH) and 9-phosphabicyclo[4.2.1]nonane (a-PhobPH) are described in detail. Selective protonation of s-PhobPH with aqueous HCl in the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Dinuclear Ruthenium Ethylene Complexes: Syntheses, Structures, and Catalytic Applications in ATRA and ATRC Reactions
Joffrey Wolf, Katrin Thommes, Oliver Briel, Rosario Scopelliti and Kay Severin
Organometallics2008 27 (17), 4464-4474
- Dinuclear Ruthenium Ethylene Complexes: Syntheses, Structures, and Catalytic Applications in ATRA and ATRC Reactions
  Joffrey Wolf, Katrin Thommes, Oliver Briel, Rosario Scopelliti and Kay Severin
  Organometallics2008 27 (17), 4464-4474
  The synthesis and structures of dinuclear Ru complexes of general formula [(arene)Ru(μ-Cl)3RuCl(L)(PR3)] are reported. Upon activation, they act as potent catalysts for atom transfer radical addition (ATRA) and cyclization (ATRC) reactions.
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