Alkene aziridination
AssigneeUniversity of Tennessee Research Foundation
InventorsDavid Matthew Jenkins, Steven Alan Cramer, Zheng Lu
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Abstract
Disclosed are metal-bound tetracarbene catalysts, such as iron based aziridination catalyst, having the formula: wherein X is a group 6, 7, 8, 9, or 10 metal and wherein Z is a hydrogen, alkyl, aryl or organic group, wherein the alkyl, aryl or organic group is optionally are independently substituted. In a specific example, a metal-bound tetracarbene catalyst has the formula: Also disclosed are methods of making (synthesizing), transmetallation reagents, these agents, metal-bound tetracarbene catalysts, and a method of catalytic alkene aziridination, using the disclosed metal-bound tetracarbene catalysts.
Claims16
A compound having the formula:
- where X is a group 6, 7, or 8 metal, and wherein Z is a hydrogen, alkyl, aryl or organic group, wherein the alkyl, aryl or organic group is optionally and independently substituted at any or all positions.
A method of making a transmetallating agent, comprising:
- contacting (Me,EtTCPh)(X)4, where X is OTf with Ag(OTf) and NEt3 in DMSO to produce the transmetallating agent
A method of making a metal bound tetracarbene catalyst, comprising:
- contacting a transmetallating reagent, comprising [{(Me,EtTCPh)Ag}2Ag2](x)4, where X is a counter ion with a group 6, 7, 8, 9, or 10 metal salt in the presence of a solvent comprising a mixture of THF and CH2Cl2.
A method of making a metal bound tetracarbene catalyst, comprising:
- contacting a transmetallating reagent, comprising [{(Me,EtTCPh)Ag}2Ag2](X)4, where X is a counter ion with a group 6, 7, 8, 9, or 10 metal salt in the presence of an organic solvent comprising tetrahydrofuran (THF).
A method of making a metal bound tetracarbene catalyst, comprising:
- contacting a tetraimidazolium precursor (Me,EtTCPh)(I)4, with a strong base to deprotonate the tetraimidazolium precursor, thereby forming a deprotonated tetraimidazolium precursor, wherein the phenyl groups of the tetraimidazolium precursor are optionally substituted;
- and
- contacting the deprotonated tetraimidazolium precursor with a solution comprising a group 6, 7, 8, or 10 metal.
A method of making a transmetallating agent, comprising:
- contacting (Me,EtTCPh)(X)4, where X is OTf or PF6 with Ag(X2) where (X2 is OTf or PF6) and NEt3 in DMSO to produce the transmetallating agent
Dependencies are inferred from the claim text.