Quinoline-oxazoline compounds and their use in oxidation synthesis
A quinoline-oxazoline compound having the formula: where one of X 1 and X 2 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 X 1 is N R2 is Z and R1 is absent, and when X 2 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.
1. 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 X 1 and X 2 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 X 1 is N R2 is Z and R1 is absent, and when X 2 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.
2. The method of claim 1 , wherein the quinoline compound is a quinoline-2-oxazoline having the formula:
3. The method of claim 2 , wherein R3 through R12 are hydrogen.
4. The method of claim 2 , wherein R3 through R8, R11 and R12 are hydrogen and R9 and R10 are methyl.
5. The method of claim 1 , wherein the quinoline compound is a 1-isoquinolineoxazoline having the formula:
6. The method of claim 5 , wherein R3 through R12 are hydrogen.
7. The method of claim 1 , wherein the quinoline compound is a 3-isoquinolineoxazoline having the formula:
8. The method of claim 7 , wherein R1 and R4 through R12 are hydrogen.
9. The method of claim 1 , wherein R1 and R3 through R12 are independently selected from the group consisting of hydrogen, lower alkyl, aryl, and halide.
10. The method of claim 9 , wherein R1 and R3 through R12 are each hydrogen.
11. The method of claim 9 , wherein at least one of R1 and R3 through R12 is methyl.
12. The method of claim 11 , wherein R9 and R10 are methyl.
13. The method of claim 9 , wherein at least one of R1 and R3 through R12 is a lower alkyl having up to 8 carbon atoms.
14. The method of claim 9 , wherein at least one of R1 and R3 through R12 is aryl.
15. The method of claim 9 , wherein at least one of R1 and R3 through R12 is a halide selected from the group consisting of fluorine, chlorine and bromine.
16. The method of claim 1 , wherein the quinolone catalyst complex further comprising the coordination center coordinated with each of the N in the quinoline compound.
17. The method of claim 16 , wherein the coordination center is a metal.
18. The method of claim 17 , wherein the metal is palladium, platinum, rhodium or nickel.
19. The method of claim 18 , wherein the palladium is palladium (II).
20. A quinoline compound having the formula:
wherein R1 and R4 through R12 are hydrogen.
21. A quinoline compound having the formula:
where one of X 1 and X 2 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 X 1 is N R2 is Z and R1 is absent, and when X 2 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.