title: CuI-mediated sequential iodination/cycloetherification of o-arylphenols: synthesis of 2- or 4-iododibenzofurans and mechanistic studies.
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.
authors.affiliation: State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, PR China.
authors.forename: Jiaji
authors.initials: J
authors.lastname: Zhao
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhang
authors.forename: Lanying
authors.initials: L
authors.lastname: Liu
authors.forename: Yimiao
authors.initials: Y
authors.lastname: He
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.forename: Juan
authors.initials: J
authors.lastname: Li
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhu
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis*; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004986:Ether / Q000737:chemistry; D054879:Halogenation; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D019800:Phenol / Q000737:chemistry*
chemical_list: D001572:Benzofurans; D007454:Iodides; D004986:Ether; D019800:Phenol; D003300:Copper; C073870:cuprous iodide; C023614:dibenzofuran