Syntheses of N-heterocyclic carbenes and intermediates therefor
AssigneeUniversity Court of the University of St Andrews
InventorsSteven P. Nolan, Sebastien Meiries
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Abstract
A method of preparing a 2,6 disubstituted anilines includes, reacting a 2-amino isophthalic acid diester with sufficient Grignard reagent R2CH2MgX to form the corresponding diol product, dehydrating the diol product to the corresponding dialkene; and hydrogenating the diol product to form the corresponding aniline. The 2,6 disubstituted anilines can be used to produce N-Heterocyclic Carbenes (NHCs). The NHCs can find application in various fields such as organic synthesis, catalysis and macromolecular chemistry. Palladium catalysts containing the NHCs are also described.
Claims14
A method of preparing an at least 2,6 disubstituted aniline, the method comprising:
- reacting a 2-amino isophthalic acid diester with sufficient Grignard reagent R2CH2MgX to form the corresponding diol product,
- wherein X is chloride, bromide or iodide, and R2 is selected from H, methyl, ethyl, n-propyl and
- wherein either R3 is H and R4 is alkyl that may be substituted, or
- each of R3, R4 are an independently selected alkyl that may be substituted;
- dehydrating the diol product to the corresponding dialkene;
- and
- hydrogenating the dialkene product to form the corresponding aniline.
An aniline of formula VII or formula VIII:
Dependencies are inferred from the claim text.