Transition metal carbene complexes containing a cationic...

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C526S172000, C502S155000, C502S167000, C546S002000, C548S101000, C544S225000

Reexamination Certificate

active

11149722

ABSTRACT:
Organometallic complexes suitable as olefin metathesis catalysts are provided. The complexes are Group 8 transition metal carbenes bearing a cationic substituent and having the general structure (I)wherein M is a Group 8 transition metal, L1and L2are neutral electron donor ligands, X1and X2are anionic ligands, m is zero or 1, n is zero or 1, and R1, W, Y, and Z are as defined herein. Methods for synthesizing the complexes are also provided, as are methods for using the complexes as olefin metathesis catalysts.

REFERENCES:
patent: 5312940 (1994-05-01), Grubbs et al.
patent: 5831108 (1998-11-01), Grubbs et al.
patent: 5969170 (1999-10-01), Grubbs et al.
patent: 6225488 (2001-05-01), Mukerjee et al.
patent: 6407190 (2002-06-01), Van der Schaaf et al.
patent: 6500975 (2002-12-01), Schwab et al.
patent: 6590048 (2003-07-01), Furstner
patent: 6803429 (2004-10-01), Morgan et al.
patent: WO 99/51344 (1999-10-01), None
patent: WO 00/58322 (2000-10-01), None
patent: WO 00/71554 (2000-11-01), None
patent: WO 03/029260 (2003-04-01), None
Audic et al., “An ionic, liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing metathesis in ionic liquids,” J. Am. Chem. Soc. (2003) 125:9248-9249.
Bassetti et al., “Rate studies and mechanism of ring closing olefin metathesis catalyzed by cationic ruthenium allenylidene arene complexes,” Organometallics (2003) 22:4459-4466.
Blackwell et al., “New approaches to olefin cross metathesis,” J. Am. Chem. Soc. (2000) 122:58-71.
Cadierno et al., “Efficient synthetic routes to terminal γ-keto-alkynes and unsaturated cyclic carbene complexes based on regio- and diastereoselective nucleophilic addition of enolates on ruthenium (II) indenyl allenylidenes,” Organometallics (2001) 20:3175-3189.
Chatterjee et al., “Synthesis of Functionalized Olefins by Cross and Ring-Closing Metatheses,”J. Am. Chem. Soc. (2000) 122(15):3783-3784.
Chatterjee et al., “Formyl vinyl C-H activation and allylic oxidation by olefin metathesis,” Angew. Chem. Intl. Ed. (2002) 41:3171-3174.
Chatterjee et al., “A general model for selectivity in olefin cross metathesis,” J. Am. Chem. Soc. (2003) 125:11360-11370.
Choi et al., “Controlled living ring opening metathesis polymerization by fast initiating ruthenium catalyst,” Angew. Chem. Intl. Ed. (2003) 42;1743-1746.
Conrad et al., “The first highly active halide-free ruthenium catalyst for olefin metathesis,” Organometallics (2003) 22:3634-3636.
De Clercq et al., “Atom transfer radical polymerization of vinyl monomers mediated by Schiff base ruthenium alkylidene catalysts and the adventitious effect of water in polymerizations with the analogous cationic complexes,” Macromol. (2002) 35:8943-8947.
Dinger et al., “High turnover numbers with ruthenium-based metathesis catalysts,” Adv. Synth. Catal. (2002) 344:671-677.
Freznel et al., “Ruthenium-based metathesis initiation: development and use in ring opening metathesis polymerization,” J. Polymer Sci. (2002) 40:2895-2916.
Furstner et al., “Comparative investigation of ruthenium-based metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands,” Chem. Eur. J. (2001) 15:3236-3253.
Garber et al., “Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts,” J. Am. Chem. Soc. (2000) 122:8168-8179.
Grubbs “Handbook of Metathesis,” vols. 1, 2 and 3, Wiley VCH, Weinheim, 2003.
Grubbs et al., “Recent advances in olefin metathesis and its application in organic synthesis,” Tetrahedron (1998) 54:4413-4450.
Harrity et al., “Ru-catalyzed rearrangement of styrenyl ethers. Enantioselective synthesis of chromenes through Zr- and Ru-catalyzed processes,” J. Am. Chem. Soc. (1997) 119:1488-1489.
Harrity et al., “Chromenes through metal-catalyzed reactions of styrenyl ethers. Mechanism and utility in synthesis,” J. Am. Chem. Soc. (1998) 120:2343-2351.
Jung et al., “Cationic vinyl and dicationic carbene ruthenium (II) complexes from a vinylidene (hydrido) precursor,” Organometallics (2001) 20:2121-2123.
Jutzi et al., “Synthesis, crystal structure, and application of the oxonium-acid [H(OEt2)2]+[B(C6F5)],” Organometallics (2000) 19:1442-1444.
Kingsbury et al., “A recyclable ruthenium-based metathesis catalyst,” J. Am. Chem. Soc. (1999) 121:791-799.
Love et al., “A practical and highly active ruthenium-based catalyst that effects cross metathesis of acrylonitrile,” (2002) Angew. Chem. Intl. Ed. 41:4035-4037.
Love et al., “Synthesis, structure and activity of enhanced initiators for olefin metathesis,” J. Am. Chem. Soc. (2003) 125:10103-10109.
Nguyen et al., “Ring-opening metathesis polymerization (ROMP) of norbornene by a group VIII carbene complex in protic media,” J. Am. Chem. Soc. (1992) 114:3974-3975.
Pruhs et al., “Preparation, reactivity and structural peculiarities of hydroxyalkyl-functionalized “second generation” ruthenium carbene complexes,” Organometallics (2004) 23:280-287.
Romero et al., “Rapidly initiating ruthenium olefin metathesis catalysts,” Angew. Chem. Int. Ed. (2004) 43:6161-6165.
Romero et al., “Direct observation of a 14-electron ruthenacyclobutane relevant to olefin metathesis,” J. Am. Chem. Soc. (2005) 127:5032-5033.
Sanford et al., “A versatile precursor for the synthesis of ruthenium olefin metathesis catalysts,” Organometallics (2001) 20:5314-5318.
Sanford et al., “Mechanism and activity of ruthenium olefin metathesis catalysts,” J. Am. Chem. Soc. (2001) 123:6543-6554.
Scholl 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,” Organic Letters (1999) 1:953-956.
Schrock “Olefin metathesis reactions catalyzed by molybdenum alkylidenes,” Tetrahedron (1999) 55:8141-8153.
Schrock “Living ring-opening metathesis polymerization catalyzed by well characterized transition metal alkylidene complexes,” Acc. Chem. Res. (1990) 23:158-165.
Schwab et al., “A series of well-defined metathesis catalysts—synthesis of [RuCl2(=CHR′)(PR3)2] and its reactions,” Angew. Chem. Intl. Ed. Engl. (1995) 34:2039-2041.
Schwab et al., “Synthesis and applications of RuCl2(=CHR′)(PR3)2: the influence of the alkylidene moiety on metathesis activity,” J. Am. Chem. Soc. (1996) 118:100-110.
Stasko et al., “Molecular structure of the solvated proton in isolated salts. Short, strong, low barrier (SSLB) H-bonds,” J. Am. Chem. Soc. (2002) 124:13869-13876.
Trnka et al., “The Development of L2X2Ru=CHR Olefin Metathesis Catalysts: An Organometallic Success Story,” Acc. Chem. Res. (2001) 34:18-29.
Volland et al., “Synthesis, structure and reactivity of cationic ruthenium (II) carbene complexes with bulky chelating bisphosphines: Design of highly active ring opening metathesis polymerization (ROMP) catalysts,” Organometallics (2004) 23:800-816.
Wakamatsu et al., “A new highly efficient ruthenium metathesis catalyst,” Angew. Chem. (2002) 114:2509-2511.
Wakamatsu et al., “A highly active and air-stable ruthenium complex for olefin metathesis,” Angew. Chem. Int. Ed. (2002) 41:794-796.
Dias et al., “Well-defined ruthenium olefin metathesis catalysts: mechanism and activity,” J. Am. Chem. Soc. (1997) 119:3887-3897.
Adhart et al., “Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry,” J. Am. Chem. Soc. (2000) 122:8204-8214.
Adhart et al., “Mechanism and activity of ruthenium olefin metathesis catalysts: the role of ligands and substrates from a theoretical perspective,” J. A

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Transition metal carbene complexes containing a cationic... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Transition metal carbene complexes containing a cationic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Transition metal carbene complexes containing a cationic... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3946803

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.