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US 2020/0038851 A1Published application
Synthesis and characterization of ru alkylidene complexes
AssigneesUmicore AG & Co. KG, California Institute of Technology
InventorsAdam M. JOHNS, Jessica R. HERRON, Richard L. PEDERSON, Bryan A. FIAMENGO, Jennifer A. BEERMAN, Tzu-Pin LIN, Crystal K. CHU, Robert H. GRUBBS
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Abstract
This invention relates generally to olefin metathesis catalyst compounds, to the preparation of such compounds, compositions comprising such compounds, methods of using such compounds, articles of manufacture comprising such compounds, and the use of such compounds in the metathesis of olefins and olefin compounds. The invention has utility in the fields of catalysts, organic synthesis, polymer chemistry, and industrial and fine chemicals industry.
Claims13
An olefin metathesis catalyst represented by Formula (I):
- wherein:
- M is ruthenium or osmium;
- X1 and X2 are independently halogen, trifluoroacetate, per-fluorophenols or nitrate;
- L1 is a ligand represented by the structure of Formula (II), or is a N-Heterocyclic Carbene ligand represented by the structure of Formula (III):
- R1 is unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene) (C5-C24 aryl)]2;
- R2 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R3 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, or substituted saturated N-heterocycle;
- Y is CR4 or N;
- R4 is hydrogen, unsubstituted (C1-C12 alkyl), or substituted (C1-C12 alkyl);
- R5 and R6 are independently hydrogen, unsubstituted (C5-C24 aryl), or substituted (C5-C24 aryl);
- Q is a two-atom linkage represented by structures —[CR7R8]s—[CR9R10]t— or —[CR11═CR12]—;
- R7, R8, R9 and R10 are independently hydrogen, unsubstituted (C1-C24 alkyl), substituted (C1-C24 alkyl), unsubstituted (C5-C24 aryl), or substituted (C5-C24 aryl);
- R11 and R12 are independently hydrogen, unsubstituted (C1-C24 alkyl), substituted (C1-C24 alkyl), unsubstituted (C5-C24 aryl), or substituted (C5-C24 aryl);
- and
- “s” and “t” are independently 1 or 2.
12 more elements
An olefin metathesis catalyst represented by the structure of Formula (IVa):
- wherein:
- X1 and X2 are independently halogen, trifluoroacetate, per-fluorophenols or nitrate;
- R1 is unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R2 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- and
- R3 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle or substituted saturated N-heterocycle.
3 more elements
A method of synthesizing an olefin metathesis catalyst represented by the structure of Formula (A):
- the method comprising contacting an olefin metathesis catalyst represented by the structure of Formula (VIII):
- with a PRdReORf ligand at room temperature in an inert solvent, wherein:
- X1 and X2 are independently halogen, trifluoroacetate, per-fluorophenols or nitrate;
- R1 is unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R2 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R3 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle or substituted saturated N-heterocycle;
- R5 and R6 are independently hydrogen, unsubstituted C5-C24 aryl, or substituted C5-C24 aryl;
- generally R5 and R6 are independently substituted C5-C24 aryl with one to three unsubstituted (C1-C6 alkyl) groups or substituted (C1-C6 alkyl) groups;
- Rd is unsubstituted C1-C10 alkyl, substituted C1-C10 alkyl, substituted C6-C10 aryl, unsubstituted C6-C10 aryl, substituted C3-C8 cycloalkyl or unsubstituted C3-C8 cycloalkyl;
- Re is unsubstituted C1-C10 alkyl, substituted C1-C10 alkyl, substituted C6-C10 aryl, unsubstituted C6-C10 aryl, substituted C3-C8 cycloalkyl or unsubstituted C3-C8 cycloalkyl;
- and
- Rf is unsubstituted C1-C10 alkyl, substituted C1-C10 alkyl, substituted C6-C10 aryl, unsubstituted C6-C10 aryl, substituted C3-C8 cycloalkyl or unsubstituted C3-C8 cycloalkyl.
9 more elements
A method of synthesizing an olefin metathesis catalyst represented by the structure of Formula (C):
- the method comprising contacting an olefin metathesis catalyst represented by the structure of Formula (IVa):
- with a N-Heterocyclic Carbene ligand of formula
- at, wherein:
- X1 and X2 are independently halogen, trifluoroacetate, per-fluorophenols or nitrate;
- R1 is unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R2 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle, substituted saturated N-heterocycle, —NH(C1-C24 alkyl), —N(C1-C24 alkyl)2, —NH(C5-C24 aryl), —N(C5-C24 aryl)2, —N(C1-C24 alkyl)(C5-C24 aryl) or —N[(C1-C6 alkylene)(C5-C24 aryl)]2;
- R3 is unsubstituted (C5-C24 aryl), substituted (C5-C24 aryl), unsubstituted saturated N-heterocycle or substituted saturated N-heterocycle;
- and
- R5 and R6 are independently hydrogen, unsubstituted C5-C24 aryl, or substituted C5-C24 aryl;
- generally R5 and R6 are independently substituted C5-C24 aryl with one to three unsubstituted (C1-C6 alkyl) groups or substituted (C1-C6 alkyl) groups.
7 more elements
Dependencies are inferred from the claim text.