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US 10,196,341 B2Granted
C-halogen bond formation
AssigneeThe Trustees of Princeton University
InventorsJohn T. Groves, Wei Liu
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.
Claims43
A method of halogenating a carbon containing compound having an sp3 C—H bond, the method comprising:
- combining the carbon containing compound, a halogenating agent comprising a halogen, a halogenating catalyst, and a phase transfer catalyst, wherein
- the halogenating catalyst is a manganese phthalocyanine, a manganese porphyrin, a manganese salophen, or a manganese porphyrazine and is present in a OH—Mn(IV)-L intermediate, where L is O, OH, or OX and X is a halide, after the step of combining, the halogenating agent is present in an amount of 1-10 equivalents based the amount of carbon containing compound, and the halogenating agent is selected from the group consisting of hypohalites, N-chlorosuccinimide (NCS), N-bromosuccinimide, hypochlorites, NaOCl, NaOBr, and calcium hypochlorite, and
- the halogen replaces the hydrogen in the sp3 C—H bond.
A method of halogenating a carbon containing compound having an sp3 C—H bond, the method comprising:
- combining the carbon containing compound, a halogenating agent comprising a halogen, a halogenating catalyst, and a phase transfer catalyst, wherein
- the halogenating catalyst is a manganese phthalocyanine, a manganese porphyrin, a manganese salophen, or a manganese porphyrazine, and after combining the halogenating catalyst comprises at least one axial ligand selected from O, OH, or OX, where X is a halide, and the halogenating agent is a hypohalite, and
- the halogen replaces the hydrogen in the sp3 C—H bond.
Dependencies are inferred from the claim text.