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US 12,098,126 B2Granted
Methods of iron catalyzed C-H bond amination
AssigneesVersitech Limited, Laboratory for Synthetic Chemistry and Chemical Biology Limited
InventorsChi-Ming Che, Tingjie You
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Abstract
Described herein is an iron(II)-phthalocyanine catalyzed C—H bond amination of alkyl azides. The catalyst is effective to produce intramolecular amination of saturated C—H bonds in moderate to excellent yields and the methods are tolerant of a wide scope of substrates. The methods described are useful for the synthesis of natural products derivatives and for the late-stage functionalization of pharmaceuticals.
Claims17
A method of C—H bond amination comprising the steps of:
- (a) forming a reaction mixture comprising an alkyl azide, an iron(II)-phthalocyanine catalyst, and one or more solvents in a reaction vessel;
- and
- (b) heating the reaction mixture to a temperature of at least about 100° C. sufficient to induce a direct intramolecular C—H bond amination of the alkyl azide;
- wherein the iron(II)-phthalocyanine catalyst is defined according to any one of Formulae A, B, C, or D:
- wherein Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, and Rj in each of Formulae A-D are each independently selected from the group consisting of a hydrogen;
- halogen group;
- a C2-C5 linear or branched alkyl group, such as a methyl, ethyl, propyl, butyl, or pentyl group;
- alkenyl group;
- alkynyl group;
- cycloalkyl group;
- cycloalkenyl group;
- cycloalkynyl group;
- a hydroxyl group;
- an alkoxy group, such as methoxy, ethoxy, propoxy, or butoxy;
- an aryl group;
- a heteroaryl group;
- a benzyl group;
- an acyl group;
- an ester group;
- a carbonyl group;
- a carboxylate group;
- an amino group;
- an amide group;
- and a nitro group.
21 more elements
Dependencies are inferred from the claim text.