Ruthenium indenylidene “1st generation” olefin metathesis catalysts containing triisopropyl phosphite

The reaction of triisopropyl phosphite with phosphine-based indenylidene pre-catalysts affords “1st generation” cis-complexes. These have been used in olefin metathesis reactions. The cis-Ru species exhibit noticeable differences with the trans-Ru parent complexes in terms of structure, thermal stability and reactivity. Experimental data underline the importance of synergistic effects between phosphites and L-type ligands.

[1]  A. Slawin,et al.  Ruthenium Olefin Metathesis Catalysts Containing Fluoride , 2015 .

[2]  C. Cazin,et al.  Phosphite ligands in Ru-based olefin metathesis catalysts , 2015, Monatshefte für Chemie - Chemical Monthly.

[3]  C. Cazin,et al.  Conducting Olefin Metathesis Reactions in Air: Breaking the Paradigm , 2015 .

[4]  César A. Urbina-Blanco,et al.  Key processes in ruthenium-catalysed olefin metathesis. , 2014, Chemical communications.

[5]  R. Goswami,et al.  Stereoselective total synthesis of cytospolide P. , 2014, The Journal of organic chemistry.

[6]  R. Reamer,et al.  Ring-closing metathesis reactions of bis(enynes): selectivity and surprises. , 2014, The Journal of organic chemistry.

[7]  K. Grela Olefin Metathesis: Theory and Practice , 2014 .

[8]  César A. Urbina-Blanco,et al.  Mixed N-Heterocyclic Carbene/Phosphite Ruthenium Complexes: The Effect of a Bulkier NHC. , 2013 .

[9]  L. Cavallo,et al.  Energetics of the ruthenium-halide bond in olefin metathesis (pre)catalysts. , 2013, Dalton Transactions.

[10]  César A. Urbina-Blanco,et al.  Synthesis and Reactivity of Ruthenium Phosphite Indenylidene Complexes , 2012 .

[11]  A. Slawin,et al.  An unusual cationic Ru(II) indenylidene complex and its Ru(III) derivative--efficient catalysts for high temperature olefin metathesis reactions. , 2012, Chemical communications.

[12]  A. Slawin,et al.  Phosphites as ligands in ruthenium-benzylidene catalysts for olefin metathesis. , 2011, Chemical communications.

[13]  C. Cazin Erratum To: N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis , 2011 .

[14]  A. Slawin,et al.  Mixed N-heterocyclic carbene/phosphite ruthenium complexes: towards a new generation of olefin metathesis catalysts. , 2010, Chemical communications.

[15]  S. Nolan,et al.  Ruthenium-indenylidene complexes: powerful tools for metathesis transformations. , 2008, Chemical communications.

[16]  F. Verpoort,et al.  Indenylidene‐Ruthenium Complexes Bearing Saturated N‐Heterocyclic Carbenes: Synthesis and Catalytic Investigation in Olefin Metathesis Reactions , 2008 .

[17]  A. Hoveyda,et al.  The remarkable metal-catalysed olefin metathesis reaction , 2007, Nature.

[18]  S. Nolan,et al.  N-heterocyclic carbene and phosphine ruthenium indenylidene precatalysts: a comparative study in olefin metathesis. , 2007, Chemistry.

[19]  T. Jamison,et al.  Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by [Ni(NHC){P(OPh)3}]: Synergy Between a Strong σ Donor and a Strong π Acceptor , 2007 .

[20]  K. C. Caster,et al.  Cross‐Linkers for Improved High Temperature Performance of ROMP Adhesives , 2007 .

[21]  Y. Chauvin,et al.  Olefin metathesis: the early days (Nobel Lecture). , 2006, Angewandte Chemie.

[22]  R. Grubbs Olefin-metathesis catalysts for the preparation of molecules and materials (Nobel Lecture). , 2006, Angewandte Chemie.

[23]  R. Schrock Multiple metal-carbon bonds for catalytic metathesis reactions (Nobel Lecture). , 2006, Angewandte Chemie.

[24]  K. Nicolaou,et al.  Metathesis reactions in total synthesis. , 2005, Angewandte Chemie.

[25]  C. Slugovc,et al.  Thermally Switchable Olefin Metathesis Initiators Bearing Chelating Carbenes: Influence of the Chelate's Ring Size , 2005 .

[26]  R. Grubbs,et al.  Latent ruthenium olefin metathesis catalysts that contain an N-heterocyclic carbene ligand , 2004 .

[27]  A. Nishida,et al.  Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-methylene-2,3-dihydroindoles and 3-methylene-2,3-dihydrobenzofurans. , 2004, Angewandte Chemie.

[28]  R. Grubbs,et al.  Decomposition of a key intermediate in ruthenium-catalyzed olefin metathesis reactions. , 2004, Journal of the American Chemical Society.

[29]  R. Schrock,et al.  Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts. , 2003, Angewandte Chemie.

[30]  R. Grubbs Handbook of metathesis , 2003 .

[31]  S. Blechert,et al.  Recent developments in olefin cross-metathesis. , 2003, Angewandte Chemie.

[32]  R. Grubbs,et al.  Mechanism and activity of ruthenium olefin metathesis catalysts. , 2001, Journal of the American Chemical Society.

[33]  R. Grubbs,et al.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story. , 2001, Accounts of chemical research.

[34]  A. Fürstner Olefin Metathesis and Beyond , 2000 .

[35]  M. Buchmeiser Homogeneous Metathesis Polymerization by Well-Defined Group VI and Group VIII Transition-Metal Alkylidenes: Fundamentals and Applications in the Preparation of Advanced Materials. , 2000, Chemical reviews.

[36]  S. Nolan,et al.  Influence of Sterically Demanding Carbene Ligation on Catalytic Behavior and Thermal Stability of Ruthenium Olefin Metathesis Catalysts , 1999 .

[37]  R. Grubbs,et al.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. , 1999, Organic letters.

[38]  W. Herrmann,et al.  N-heterocyclic carbenes: novel ruthenium–alkylidene complexes , 1999 .

[39]  R. Grubbs,et al.  Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes. , 1997, The Journal of organic chemistry.

[40]  J. Ziller,et al.  Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity , 1996 .

[41]  Robert H. Grubbs,et al.  Ring-Closing Metathesis and Related Processes in Organic Synthesis , 1995 .

[42]  S. Nguyen,et al.  Syntheses and activities of new single-component, ruthenium-based olefin metathesis catalysts , 1993 .

[43]  S. Nguyen,et al.  Ring-opening metathesis polymerization (ROMP) of norbornene by a Group VIII carbene complex in protic media , 1992 .