Mild, Efficient, and Highly Regioselective Synthesis of 2,6-Diiodobenzaldehyde Derivatives
| Autor: | Walid K. Al-Jammal, Robert McDonald, Khaled T. Jaradat, Raed M. Al-Zoubi |
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| Rok vydání: | 2020 |
| Předmět: | |
| Zdroj: | Synlett. 31:953-958 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/s-0040-1708004 |
| Popis: | An efficient and versatile synthesis of 2,6-diiodobenzaldehydes via highly regioselective metal–iodine exchange (MIE) of 5-substituted 1,2,3-triiodobenzenes is reported. The nature of substituents (R) on the phenyl has a large influence on the reactivity of reaction but not on the regioselectivity. The regioselectivity of the MIE can be controlled by the use of ethyl formate as a formylating agent providing only the internal benzaldehyde derivatives in excellent site-selectivity. The best reactivity and the highest isolated yields were furnished with products bearing electron-rich substituents. Several chemical transformations of the target compound as a valuable precursor in synthesis were also demonstrated providing the desired derivatives in good isolated yields. This report discloses a protocol for the synthesis of 2,6-diiodobenzaldehyde derivatives that is scalable, general in scope, and indeed difficult to be made by other means. |
| Databáze: | OpenAIRE |
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