Quinoline-oxazoline compounds and their use in oxidation synthesis
AssigneeUniversity of Utah Research Foundation
InventorsMatthew Scott Sigman, Brian William Michel
Life of this patent
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Abstract
A quinoline-oxazoline compound having the formula: where one of X1 and X2 is N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula such that when X1 is N R2 is Z and R1 is absent, and when X2 is N either R1 or R3 is Z and R2 is absent. R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center. These compounds can be complexed with a suitable coordination center such as catalytically active palladium and can be highly useful in catalytically oxidizing alkenes with high regioselectivity.
Claims21
A method of catalytically oxidizing an alkene, comprising:
- a) exposing an alkene to a quinoline catalyst complex in the presence of a mediation compound to form a ketone, said quinoline catalyst complex including a coordination center complexed with a quinoline compound having the formula
- where one of X1 and X2 is an N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline having the formula
- such that when X1 is N R2 is Z and R1 is absent, and when X2 is N either R1 or R3 is Z and R2 is absent, and R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with the coordination center.
A quinoline compound having the formula:
- wherein R1 and R4 through R12 are hydrogen.
A quinoline compound having the formula:
- where one of X1 and X2 is an N and the other is C and one of R1, R2 and R3 is Z wherein Z is an oxazoline radical having the formula
- such that when X1 is N R2 is Z and R1 is absent, and when X2 is N either R1 or R3 is Z and R2 is absent, and R1 and R3 through R12 are independently H or a pendant moiety which does not interfere with coordination of either N in the quinoline compound with a coordination center and at least one of R1 and R3 through R12 is a halide selected from the group consisting of fluorine, chlorine and bromine.
Dependencies are inferred from the claim text.