Nucleophilic Addition of Benzylboronates to Activated Ketones
| Autor: | Michael R. Hollerbach, Timothy J. Barker, Jacob C. Hayes |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Nucleophilic addition Ketone 010405 organic chemistry Pinacol Organic Chemistry DABCO 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Aldehyde Article 0104 chemical sciences chemistry.chemical_compound chemistry Amide Drug Discovery Electrophile Chemoselectivity |
| Zdroj: | Tetrahedron Lett |
| ISSN: | 0040-4039 |
| Popis: | A method has been developed for the addition of benzylboronic acid pinacol ester to activated ketones including trifluoromethyl ketones in good yields. The use of DABCO as an additive was found to enhance the rate and efficiency of this reaction. In reactions of ketones with a second carbonyl group present such as an ester or amide, good chemoselectivity for the ketone was observed. Competition experiments suggest an electrophile relative reactivity order of CF(2)H ketone > CF(3) ketone > aldehyde under these reaction conditions. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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