C-halogen bond formation
AssigneeThe Trustees of Princeton University
InventorsJohn T. Groves, Wei Liu, Xiongyi Huang
Life of this patent
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Abstract
Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.
Claims20
A method of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond to form an sp3 C-F bond, the method comprising:
- mixing a fluorinating catalyst, a fluorinating agent, and the carbon containing compound in an organic solvent to form a first mixture;
- providing an inert gas over the first mixture;
- and
- adding an oxidant to the first mixture to form a second mixture,
- wherein the fluorinating agent is a fluoride ion source.
A composition comprising at least one compound selected from the group consisting of 3-fluoro-5α-cholestane;
- 2- and 3-fluoro-sclareolide;
- 1, 3, 5(10)-estratrien-17-one;
- fluoro-(1R,4aS, 8aS)-octahydro-5,5,8a-trimethyl-1-(3-oxobutyl)-naphthalenone;
- (1R, 4S, 6S,10S)-4,12,12-trimethyl-tricyclo[8.2.0.04,6]dodecan-9-one;
- fluoro-levomethorphan;
- fluoro-lupine;
- fluoro-20-methyl-5alpha(H)-pregnane;
- fluoro-isolongifolanone;
- fluoro-caryophyllene acetate;
- fluoro-N-acetylgabapentin methyl ester;
- fluoro-acetyl-amantidine;
- phthalimido-fluoro-amantadine;
- methylene-fluorinated methyloctanoate;
- methylene fluorinated saturated fatty acid esters;
- N-acetyl-fluoro-Lyrica methyl ester;
- fluoro-artemisinin, fluoro-adapalene;
- fluoro-finasteride;
- N-acetyl-methyl-fluoro-phenidate;
- fluoro-mecamylamine;
- N-acetyl-fluoro-mecamylamine;
- N-acetyl-fluoro-memantine;
- hthalimido-fluoro-memantine;
- N-acetyl-fluoro-enanapril precursor methyl ester;
- fluoro-progesterone;
- fluoro-dopamine derivative;
- fluoro-pregabalin;
- fluoro-cholestane;
- methyl-fluoro-phenidate derivative;
- fluoro-gabapentin;
- fluoro-memantine derivative;
- fluoro-rimantadine derivative;
- fluoro-tramadol;
- fluoro-enalapril precursor;
- fluoro-donepezil precursor;
- fluoro-amphetamine;
- fluoro-tocopherol form of vitamin E;
- fluoro-melatonin;
- homophenylalanine;
- DOPA;
- fluoro-ibuprofen methyl ester;
- fluoro-buspirone;
- fluoro-eticyclidine;
- fluoro-amantadine;
- fluoro-lubiprostone;
- fluoro-penridopril;
- fluoro-fosinopril;
- fluoro-2-adamantanone;
- fluoro-rimantadine analogue;
- fluoro-adapalene precursor;
- fluoro-perindopril precursor;
- protected fluoro-gabapentin;
- methyl fluoro-octanoate;
- methyl fluoro-nonanate;
- methyl fluoro-hexanoate;
- fluoro-cyclohexyl acetate;
- and fluoro-cyclohexane carboxylic acid methyl ester;
- or an analog of any of the foregoing.
A composition comprising a trans-difluoromanganese(IV) porphyrin MnIV(TMP)F2.
A composition comprising at least two or more of a carbon containing compound having an sp3 C—H bond, a fluorinating agent, a fluorinating catalyst, or an oxidant.
Dependencies are inferred from the claim text.