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US 12,049,449 B2Granted
Methods of hydromethylation of alkenes and ketones
AssigneeThe Florida State University Research Foundation, Inc.
InventorsJames H. Frederich, James A. Law
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Abstract
Methods of hydromethylation of alkenes and ketones, including methods that use Tebbe's reagent. The methods may include contacting Cp2Ti(μ-Cl)(μ-CH2)AlMe2 and an alkene or a ketone to produce an intermediate product that may include a titanacyclobutane. The intermediate product may be contacted with an acid to produce a methylated product.
Claims17
A method of hydromethylation, the method comprising:
- contacting (i) an alkene, and (ii) Cp2Ti(μ-Cl)(μ-CH2)AlMe2 to produce an intermediate product in a reaction mixture;
- and
- contacting the intermediate product with an acid to produce a methylated product, wherein the intermediate product is not isolated from the reaction mixture prior to the contacting of the intermediate product with the acid;
- wherein the alkene has a structure according to formula (I)—
- wherein R1 is a C1-C20 hydrocarbyl, and R2 and R3 are hydrogen,
- wherein the methylated product includes (i) a first product in which the carbon atom bonded to R1 and R2 is methylated, and (ii) a second product in which the carbon atom bonded to R3 is methylated, and
- wherein a mole ratio of the first product to the second product is about 3:1 to about 30:1.
4 more elements
A method of hydromethylation, the method comprising:
- contacting (i) an alkene, and (ii) Cp2Ti(μ-Cl)(μ-CH2)AlMe2 at a temperature less than 30° C. in the presence of a Lewis base to produce an intermediate product in a reaction mixture, the intermediate product comprising a titanacyclobutane moiety;
- and
- contacting the intermediate product with an acid to produce a methylated product, wherein the intermediate product is not isolated from the reaction mixture prior to the contacting of the intermediate product with the acid;
- wherein the alkene has a structure according to formula (I)—
- wherein R1 is a C1-C20 hydrocarbyl, and R2 and R3 are hydrogen,
- wherein the methylated product includes (i) a first product in which the carbon atom bonded to R1 and R2 is methylated, and (ii) a second product in which the carbon atom bonded to R3 is methylated, and
- wherein a mole ratio of the first product to the second product is about 3:1 to about 30:1.
4 more elements
Dependencies are inferred from the claim text.