CuI-Mediated Sequential Iodination/Cycloetherification of o-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies

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• 作者：Jiaji Zhao ; Qi Zhang ; Lanying Liu ; Yimiao He ; Jing Li ; Juan Li ; Qiang Zhu
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：October 19, 2012
• 年：2012
• 卷：14
• 期：20
• 页码：5362-5365
• 全文大小：262K
• 年卷期：v.14,no.20(October 19, 2012)
• ISSN：1523-7052

文摘

An efficient synthesis of 2- or 4-iododibenzofurans through CuI-mediated sequential iodination/cycloetherification of two aromatic C鈥揌 bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO₂, CN, and CHO) and the newly introduced iodide are readily modified for a focused dibenzofuran library synthesis. Mechanistic studies and DFT calculations suggest that a Cu(III)-mediated rate-limiting C鈥揌 activation step is involved in cycloetherification.