化学
合成子
碘
酚类
卤化
电泳剂
碘化物
碘化铵
部分
组合化学
有机化学
催化作用
作者
Yuvraj Satkar,Luisa F. Yera-Ledesma,Narendra Mali,Dipak Patil,Pedro Navarro‐Santos,Luis A. Segura‐Quezada,Perla I. Ramírez-Morales,César R. Solorio‐Alvarado
标识
DOI:10.1021/acs.joc.9b00161
摘要
An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive “I+” synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
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