Organic Letters 2012-10-19

CuI-mediated sequential iodination/cycloetherification of o-arylphenols: synthesis of 2- or 4-iododibenzofurans and mechanistic studies.

Jiaji Zhao, Qi Zhang, Lanying Liu, Yimiao He, Jing Li, Juan Li, Qiang Zhu

Index: Org. Lett. 14(20) , 5362-5, (2012)

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Abstract

An efficient synthesis of 2- or 4-iododibenzofurans through CuI-mediated sequential iodination/cycloetherification of two aromatic C-H bonds in o-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO(2), 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-H activation step is involved in cycloetherification.