Iridium-Catalyzed Cage B(4)-Amidation Reaction of o-Carboranes with Dioxazolones: Selective Synthesis of Amidated o-Carboranes and Amidated and Methoxycarbonylated nido-Carboranes
| Autor: | Phil Ho Lee, Kyungsup Lee, Hee Chan Noh, Seohyun Shin, Yonghyeon Baek, Gi Uk Han |
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| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Decarboxylation Carboxylic acid Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Iridium Physical and Theoretical Chemistry Trimethylsilyldiazomethane Cage |
| Zdroj: | Organic Letters. 23:416-420 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c03927 |
| Popis: | Described is the Ir-catalyzed cage B(4)-amidation of o-carboranes with dioxazolones by carboxylic acid-assisted B(4)-H bond activation under extremely mild conditions, affording amidated o-carboranes and amidated and methoxycarbonylated nido-carboranes through sequential B(4)-amidation, O-methylation, and B(3)-deboronation in one pot. Carboxylic acid used as a directing group after the cage B(4)-amidation is efficiently trapped by trimethylsilyldiazomethane instead of undergoing decarboxylation. Mechanism studies demonstrated that the O-methylation through trapping of acid occurred first, followed by the B(3)-deboronation. |
| Databáze: | OpenAIRE |
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