Catalytic Halogen Bond Activation in the Benzylic C-H Bond Iodination with Iodohydantoins
| Autor: | Heike Hausmann, Lijuan Song, Peter R. Schreiner, Abolfazl Hosseini, Sascha H. Combe |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Halogen bond Proton 010405 organic chemistry Carboxylic acid Organic Chemistry chemistry.chemical_element Halogenation 010402 general chemistry Photochemistry Iodine 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry Radical initiator Reactivity (chemistry) Physical and Theoretical Chemistry |
| Zdroj: | Organic letters. 19(22) |
| ISSN: | 1523-7052 |
| Popis: | This letter presents the side-chain iodination of electron-deficient benzylic hydrocarbons at rt using N-hydroxyphthalimide (NHPI) as radical initiator and 1,3-diiodo-5,5-dimethylhydantoin and 3-iodo-1,5,5-trimethylhydantoin (3-ITMH) as iodine source. Addition of a carboxylic acid increased the reactivity due to complex formation with and activation of 3-ITMH by proton transfer and halogen bond formation. No SEAr reactions were observed under the employed reaction conditions. Our method enables convenient product isolation and gives 50–72% yields of isolated products. |
| Databáze: | OpenAIRE |
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