Preparation of saturated imidazolinium salts and related compounds
AssigneesMateria, Inc., California Institute of Technology
InventorsKevin Kuhn, Robert H. Grubbs
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Abstract
Methods for the preparation of saturated imidazolinium salts and related compounds that comprises reaction of formamidines with compounds such as dihaloethane and an optional base are disclosed. Alternatively, the imidazolinium salts and related compounds can be prepared in a one-step process without purification of the formamidine reactant. These methods make it possible to obtain numerous imidazolinium salts and related compounds under solvent-free reaction conditions and in excellent yields.
Claims18
A method of preparing a compound of formula (III), comprising the steps of:
- reacting a formamidine of formula (I) with a compound of formula (II) to form a compound of formula (III), according to the following reaction:
- wherein:
- Ar in each occurrence is independently selected from the group consisting of phenyl, naphthyl and anthracenyl;
- R1 in each occurrence is independently selected from the group consisting of C1-C6 alkyl;
- C1-C6 alkoxy;
- halogen;
- aryl;
- —Si(R2)3, wherein each R2 is independently a C1-C6 alkyl;
- and —NR3R4, wherein R3 and R4 are independently a C1-C6 alkyl or wherein R3 and R4, together with the nitrogen carrying them form a 5- or 6-membered heterocyclic ring;
- X is a leaving group;
- each n ranges from 0 to 5 when Ar is phenyl, from 0 to 7 when Ar is naphthyl, and from 0-9 when Ar is anthracenyl;
- and
- p ranges from 2 to 5.
A one-step method of preparing a compound of formula (III) comprising the step of:
- reacting a compound of formula (IV) and trialkyl orthoformate of formula (V) in the presence of a compound of formula (II) to form a compound of formula (III), according to the following reaction:
- wherein:
- Ar is selected from the group consisting of phenyl, naphthyl and anthracenyl;
- R1 in each occurrence is independently selected from the group consisting of C1-C6 alkyl;
- C1-C6 alkoxy;
- halogen;
- aryl;
- —Si(R2)3, wherein each R2 is independently a C1-C6 alkyl;
- and —NR3R4, wherein R3 and R4 are independently a C1-C6 alkyl or wherein R3 and R4, together with the nitrogen carrying them form a 5- or 6-membered heterocyclic ring;
- X is a leaving group;
- each n ranges from 0 to 5 when Ar is phenyl, from 0 to 7 when Ar is naphthyl, and from 0-9 when Ar is anthracenyl;
- R5 is a C1-C6 alkyl;
- and
- p ranges from 2 to 5.
Dependencies are inferred from the claim text.