Recent advances in olefin metathesis by molybdenum and tungsten imido alkylidene complexes

Abstract Recent advances in olefin metathesis studies include the preparation of catalysts “in situ,” supported catalysts, and tungsten-based catalysts, and observation of molybdacyclobutane complexes, molybdacyclopentane complexes, base-free methylene complexes, and ethylene complexes such as Mo(N-2,6-Cl2C6H3)(CH2CH2)[rac-Biphen](Et2O).

[1]  T. J. Katz,et al.  Metathesis of a cyclic trisubstituted alkene. Preparation of polyisoprene from 1-methylcyclobutene , 1976 .

[2]  C. Cummins,et al.  Facile Synthesis of Trialkoxymolybdenum(VI) Alkylidyne Complexes for Alkyne Metathesis , 2000 .

[3]  M. Leconte,et al.  A Cyclometalated Aryloxy(chloro)neopentylidenetungsten Complex: A Highly Active and Stereoselective Catalyst for the Metathesis of cis‐ and trans‐2‐Pentene, Norbornene, 1‐Methyl‐norbornene, and Ethyl Oleate , 1992 .

[4]  R. Schrock,et al.  New Chiral Molybdenum Catalysts for Asymmetric Olefin Metathesis that Contain 3,3‘-Disubstituted Octahydrobinaphtholate or 2,6-Dichlorophenylimido Ligands , 2002 .

[5]  Joseph C. Calabrese,et al.  Synthesis and crystal structure of diphenylcarbene(pentacarbonyl)tungsten(0) , 1977 .

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

[7]  R. Schrock,et al.  Multiple metal-carbon bonds. 7. Preparation and characterization of Ta(.eta.5-C5H5)2(CH2)(CH3), a study of its decomposition, and some simple reactions , 1978 .

[8]  C. Casey,et al.  Diphenylcarbene)pentacarbonyltungsten(0) , 1973 .

[9]  U. Bunz,et al.  Alkyne Metathesis with Simple Catalyst Systems: Efficient Synthesis of Conjugated Polymers Containing Vinyl Groups in Main or Side Chain , 2000 .

[10]  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.

[11]  R. Schrock.  Multiple metal-carbon bonds. 5. The reaction of niobium and tantalum neopentylidene complexes with the carbonyl function , 1976 .

[12]  T. J. Katz,et al.  Metathesis of cyclic and acyclic olefins , 1977 .

[13]  D. Goldberg,et al.  Acrylonitrile Cross-Metathesis: Coaxing Olefin Metathesis Reactivity from a Reluctant Substrate , 1995 .

[14]  R. Schrock,et al.  Multiple metal-carbon bonds. 16. Tungsten-oxo alkylidene complexes as olefins metathesis catalysts and the crystal structure of W(O)(CHCMe3(PEt3)Cl2 , 1980 .

[15]  R. Schrock,et al.  Metallacyclopentane to metallacyclobutane ring contraction , 1979 .

[16]  A. Fürstner,et al.  Mo[N(t-Bu)(Ar)]3 Complexes As Catalyst Precursors: In Situ Activation and Application to Metathesis Reactions of Alkynes and Diynes , 1999 .

[17]  Richard R. Schrock,et al.  Alkylcarbene complex of tantalum by intramolecular .alpha.-hydrogen abstraction , 1974 .

[18]  A. Fürstner,et al.  Ring-Closing Alkyne Metathesis: Application to the Stereoselective Total Synthesis of Prostaglandin E2-1,15-Lactone , 2000 .

[19]  R. Schrock.  High-oxidation-state molybdenum and tungsten alkylidyne complexes , 1986 .

[20]  F. Lefebvre,et al.  Aryloxy complexes and cyclometallated aryloxy alkylidene complexes of tungsten (VI). Application to the metathesis of functionalized olefins , 1995 .

[21]  R. Schrock,et al.  Metathesis of acetylenes by tungsten(VI)-alkylidyne complexes , 1981 .

[22]  T. J. Katz,et al.  Mechanism of the olefin metathesis reaction , 1975 .

[23]  J. Dewan,et al.  Multiple metal-carbon bonds. 43. Well-characterized, highly active, Lewis acid free olefin metathesis catalysts , 1986 .

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

[25]  A. Shusterman,et al.  REACTIONS OF BENZYLIDENE PENTACARBONYLTUNGSTEN WITH ALKENES , 1979 .

[26]  A. Fürstner,et al.  Ring-Closing Metathesis of Functionalized Acetylene Derivatives: A New Entry into Cycloalkynes. , 1998, Angewandte Chemie.

[27]  G. Bazan,et al.  Reduction of molybdenum imido-alkylidene complexes in the presence of olefins to give molybdenum(IV) complexes , 1991 .

[28]  J. Sancho,et al.  Tantalacyclopentane complexes and their role in the catalytic dimerization of olefins , 1980 .

[29]  J. Dewan,et al.  Preparation and reactivity of several alkylidene complexes of the type W(CHR')(N-2,6-C6H3-iso-Pr2)(OR)2 and related tungstacyclobutane complexes. Controlling metathesis activity through the choice of alkoxide ligand , 1988 .

[30]  R. Schrock,et al.  Evaluation of Enantiomerically Pure Binaphthol-Based Molybdenum Catalysts for Asymmetric Olefin Metathesis Reactions that Contain 3,3‘-Diphenyl- or 3,3‘-Dimesityl-Substituted Binaphtholate Ligands. Generation and Decomposition of Unsubstituted Molybdacyclobutane Complexes , 2001 .

[31]  Matthias Schuster,et al.  Olefin Metathesis in Organic Chemistry , 1997 .

[32]  K. J. Ivin,et al.  Olefin metathesis and metathesis polymerization , 1997 .

[33]  R. Grubbs,et al.  The development of well-defined catalysts for ring-opening olefin metathesis polymerizations (ROMP) , 1992 .

[34]  U. Bunz,et al.  Alkyne Metathesis as a New Synthetic Tool: Ring-Closing, Ring-Opening, and Acyclic. , 1999, Angewandte Chemie.

[35]  G. Bazan,et al.  Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefins , 1990 .

[36]  R. Schrock.  THE ALKOXIDE LIGAND IN OLEFIN AND ACETYLENE METATHESIS REACTIONS , 1995 .

[37]  Alois Fürstner.  Olefin Metathesis and Beyond , 2000 .

[38]  R. Schrock,et al.  Preparation and characterization of tantalum(III) olefin complexes and tantalum(V) metallacyclopentane complexes made from acyclic .alpha. olefins , 1979 .

[39]  C. Casey,et al.  Reactions of (diphenylcarbene)pentacarbonyltungsten(0) with alkenes. Role of metal-carbene complexes in cyclopropanation and olefin metathesis reactions , 1974 .

[40]  W. Crowe,et al.  Highly selective cross-metathesis of terminal olefins , 1993 .

[41]  R. Schrock,et al.  Multiple metal-carbon bonds. 19. How niobium and tantalum complexes of the type M(CHCMe3)(PR3)2Cl3 can be modified to give olefin metathesis catalysts , 1981 .

[42]  Y. Imamoğlu.  Metathesis polymerization of olefins and polymerization of alkynes , 1998 .

[43]  A. Fürstner,et al.  Ring Closing Alkyne Metathesis. Comparative Investigation of Two Different Catalyst Systems and Application to the Stereoselective Synthesis of Olfactory Lactones, Azamacrolides, and the Macrocyclic Perimeter of the Marine Alkaloid Nakadomarin A , 1999 .

[44]  R. Schrock,et al.  Catalytic Enantioselective Ring-Closing Metathesis by a Chiral Biphen−Mo Complex , 1998 .

[45]  D. Goldberg,et al.  Preparation of allylsilanes via cross-metathesis , 1996 .

[46]  Robert H. Grubbs,et al.  Recent advances in olefin metathesis and its application in organic synthesis , 1998 .