Continuous metathesis reactions by molybdenum carbene complexes supported on inorganic carriers

Preishuber‐Pflügl, Peter; Eder, Elisabeth; Stelzer, Franz

doi:10.1515/epoly.2002.2.1.619

Cited by 5 publications

(6 citation statements)

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“…While various supported versions of MoO 3 -based catalysts are widely used in industrial petrochemical processes including the SHOP process, 169,170 supported versions of well-defined catalysts, i.e., analogues of Schrock catalysts, are rare. Significant ROMP activity was observed under continuous conditions; 158 nevertheless, the actually active species remained unknown, and cis/trans selectivities opposite to the ones found with similar complexes in solution were observed.…”

Section: Immobilization Through the Alkoxide Ligandmentioning

confidence: 83%

“…This route has extensively been used for immobilization of Schrock catalysts on inorganic supports. [158][159][160] Nevertheless, only recent approaches by the groups of Schrock, Basset, and Cope ´ret allowed for realizing well-defined systems. [161][162][163][164][165][166][167] The silica-supported, Mo(t-BuArN) 3 (CCEt)-derived alkyne metathesis catalyst described by Moore et al also deserves to be mentioned here.…”

Section: General Considerationsmentioning

confidence: 99%

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Polymer-Supported Well-Defined Metathesis Catalysts

2008

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Section: Immobilization Through the Alkoxide Ligandmentioning

confidence: 83%

Section: General Considerationsmentioning

confidence: 99%

Polymer-Supported Well-Defined Metathesis Catalysts

2008

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“…TONs in the range of 4-20 were reported. 79 Significant ROMP activity was observed under continuous conditions, 80 nevertheless, the actual active species remained unknown and cis/trans selectivities opposite to the ones found with similar complexes in solution were observed.…”

Section: Ruthenium-based Systemsmentioning

confidence: 99%

Recent advances in the synthesis of supported metathesis catalysts

Buchmeiser

2004

New J. Chem.

134

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The state of the art and recent developments in the synthesis of supported, well-defined metathesis catalysts are reviewed. In this context, their synthesis, selected properties and application to both polymer and organic chemistry are summarised. Special consideration will be given to aspects of activity [discussed in terms of turnover numbers (TONs) and turn over frequencies (TOFs)], regioselectivity and enantioselectivity as well as stability. The general applicability of these supported catalysts to either high-throughput technology or to the manufacture of continuous flow systems is discussed.

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“…Mo{N[2,6-Me 2 -4(6-BrC 6 H 12 )]C 6 H 2 }(CHCMe 2 C 6 H 5 )-A C H T U N G T R E N N U N G (OTf) 2 A C H T U N G T R E N N U N G (DME) (19) Compound 15 (0.972 g, 1.049 mmol) was dissolved in 100 mL of dimethoxyethane (DME) and the solution was cooled to À38 8C. Triflic acid (0.472 g, 3.15 mmol) diluted in 10 mL of DME and chilled to À38 8C was added and the mixture was stirred for 12 h. The volatile components were removed under vacuum and the solid was re-dissolved in diethyl ether and filtered.…”

Section: Mo{na C H T U N G T R E N N U N G [26-a C H T U N G T R E Nmentioning

confidence: 99%

Polymer‐Supported Chiral Schrock Catalysts Immobilized via the Arylimido Ligand

et al. 2006

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The immobilization of both chiral and non-chiral versions of the Schrock catalyst via the arylimido ligand was accomplished for the first time. For this purpose, four different 4-(6-halogenohexyl)-2,6-R 2 -anilines, i.e., {4-[6-X-(CH 2 ) 6 ]-2,6-R 2 -C 6 H 2 -NH 2 } (7: R= Me, X = Br; 8: R= Me, X = Cl, 9: R= 2-Pr, X = Cl, 10: R= 2-Pr, X = Br) were prepared and used for the synthesis of the corresponding MobisA C H T U N G T R E N N U N G (imido)dichloro complexes Mo{N-2,6-R 2 -4-[6-X-(CH 2 ) 6 ]-C 6 H 2 } 2 Cl 2 ·DME (11: R= Me, X = Br; 12: R = Me, X = Cl; 13: R= 2-Pr, X = Cl; 14: R= 2-Pr, X = Br). Compounds 11-14 were transformed into the corresponding Mo-bisA C H T U N G T R E N N U N G (imido)dialkyl complexes Mo{N-2,6-R 2 -4-[6-X-(CH 2 ) 6 ]-C 6 H 2 } 2 (CH 2 CMe 2 Ph) 2 (15: R= Me, X = Br; 16: R= Me, X = Cl, 17: R= 2-Pr, X = Cl; 18: R= 2-Pr, X = Br). These were used for the synthesis of the Mo-imidoalkylidene triflates·DME (19: R= Me, X = Br; 20: R= 2-Pr, X = Br, 21: R= 2-Pr, X = Cl). Compounds 19--21 were used in the synthesis of the Schrock type catalysts H T U N G T R E N N U N G (CHCMe 2 Ph)[OC-A C H T U N G T R E N N U N G (CH 3 )A C H T U N G T R E N N U N G (CF 3 ) 2 ] (23), Mo{N-2,6-Me 2 -4-[6-Br-(CH 2 ) 6 ]-C 6 H 2 }A C H T U N G T R E N N U N G (CHCMe 2 Ph)[(R)-BIPHEN] (24) and MoA C H T U N G T R E N N U N G {N-2,6-A C H T U N G T R E N N U N G (2-Pr) 2 -4-[6-Br-(CH 2 ) 6 ]-C 6 H 2 }A C H T U N G T R E N N U N G (CHCMe 2 Ph)[(R)-BIPHEN] (25). Compounds 22, 24and 25 were immobilized on Ag-perfluoroalkylsulfonate-modified PS-and PS-DVB materials to yield the corresponding immobilized catalysts Mo{N-2,6-Me 2 -4-28). These were used in a series of ring-closing metathesis (RCM), ringopening cross metathesis, asymmetric RCM and desymmetrization reactions. The use of 27 and 28 resulted in values for enantiomeric excess (ee) virtually identical to those obtained with the corresponding homogeneous chiral catalysts.

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Continuous metathesis reactions by molybdenum carbene complexes supported on inorganic carriers

Cited by 5 publications

References 0 publications

Polymer-Supported Well-Defined Metathesis Catalysts

Polymer-Supported Well-Defined Metathesis Catalysts

Recent advances in the synthesis of supported metathesis catalysts

Polymer‐Supported Chiral Schrock Catalysts Immobilized via the Arylimido Ligand

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