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US 2019/0161457 A1Published application
Solid-supported catalyst for cross-coupling
AssigneeKing Fahd University of Petroleum and Minerals
InventorsBassam El Ali, Rami Khalid Suleiman, Mansur Bala Ibrahim
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Abstract
A solid-supported catalyst ligand which chelates palladium (II) species to form a complex that functions as a heterogeneous catalyst that is stable and can be recycled without significantly losing any catalytic activity in a variety of chemical transformations, a method for producing the solid-supported catalyst ligand and a method for catalyzing a palladium cross-coupling reaction, such as the Suzuki-Miyaura, Mizoroki-Heck, and Sonagashira reactions.
Claims10
1:
- A solid-supported catalyst, comprising:
- a catalytic metal in the form of a Pd+2 species having the formula PdZ2, wherein Z is selected from the group consisting of —Cl, —I, —Br, —OAc, and —OTf, and
- a solid-supported ligand of formula (I)
- wherein the nitrogen atoms of the two oxazoline heterocycles of the solid-supported ligand chelate the catalytic metal;
- and
- wherein R1, R2, R3 and R4 are independently —H, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
- each R5 and R6 is independently —H, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;
- X is O, NH, or S;
- and
- wherein SS is a solid resin bead with the proviso that the solid resin bead is not silica.
7 more elements
2:
- The solid-supported catalyst of claim 1, wherein the solid resin bead is Merrifield resin.
3:
- The solid-supported catalyst of claim 1, wherein the solid-supported ligand of formula (I) is
(canceled)
5:
- The solid-supported catalyst of claim 1, wherein the solid-supported catalyst is in the form of a particle having an average particle size in terms of an average diameter of 1-100 μm.
6:
- (canceled)
7:
- The solid-supported catalyst of claim 1, wherein
- R1 and R2 is —CH3;
- R3, R4, R5, and R6 is —H;
- X is O;
- and
- the Pd+2 species having the formula PdZ2 is PdCl2.
3 more elements
8:
- The solid-su ported catalyst of claim 1, which comprises 0.05-1.5 mmol of palladium per gram of the catalyst composition.
9:
- The solid-supported catalyst of claim 1, which has a turnover number in a range of 1500-2500 and a turnover frequency in a range of 200-1500 per hour.
10-20. (canceled)
Dependencies are inferred from the claim text.