Selective nitrogen functionalization of organic compounds
AssigneeF2 Chemicals Limited
InventorsRichard Dickinson Chambers, Mandy Parsons, Graham Sandford
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Abstract
There is provided a method of selectively replacing a carbon-hydrogen bond at an unactivated saturated sp3 hybridised carbon atom in an organic compound by a carbon-nitrogen bond, the method comprising reacting the compound with a fluorinating agent in a solvent reaction medium comprising a nitrile compound and providing a Lewis acid whereby the carbon-hydrogen bond is replaced by a carbon-nitrogen bond. Advantageously, the reaction may be performed in one stage and/or in one vessel. Advantageously, the method may be carried out at or just below ambient or room temperature.
Claims10
A method of selectively replacing a carbon-hydrogen bond at an unactivated saturated Sp3 hybridised carbon atom in an organic compound by a carbon-nitrogen bond, the method comprising reacting the compound with a fluorinating agent in a solvent reaction medium comprising a nitrile compound and providing a Lewis acid whereby the carbon-hydrogen bond is replaced by a carbon-nitrogen bond.
A method according to any one preceding claim wherein the nitrile compound is selected from acetonitrile and propionitrile.
A method according to one preceding claim wherein the solvent reaction medium mainly comprises nitrile compound.
A method according to any one preceding claim wherein the Lewis acid comprises boron trifluoride.
A method according to any one preceding claim wherein the molar ratio of the Lewis acid to the organic compound is in the range from 0.5:1 to 10:1.
A method according to any one preceding claim wherein the Lewis acid is added to the solvent reaction medium after reacting the compound with the fluorinating agent.
A method according to any preceding claim wherein the organic compound is selected from the group consisting of compounds 1,5 and 6 as follows:
- and whereby the replacement by a carbon-nitrogen bond produces the corresponding compound 2,3 or 4 as follows:
- wherein the groups R1, R2, R3, R4, R5, R6 and R7 are independently selected from hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl and where any of the groups R1, R2, R3, R4, R5, R6 and R7 is an alkyl, cycloalkyl or aryl substituent, the group optionally including one or more substituents or hetero-atoms and the n values are independently integers in the inclusive range from 1 to 8.
Dependencies are inferred from the claim text.