CuI-Mediated Sequential Iodination/Cycloetherification of <i>o</i>‑Arylphenols: Synthesis of 2- or 4‑Iododibenzofurans and Mechanistic Studies
Jiaji Zhao
Qi Zhang
Lanying Liu
Yimiao He
Jing Li
Juan Li
Qiang Zhu
10.1021/ol302562a.s001
https://acs.figshare.com/articles/journal_contribution/CuI_Mediated_Sequential_Iodination_Cycloetherification_of_i_o_i_Arylphenols_Synthesis_of_2_or_4_Iododibenzofurans_and_Mechanistic_Studies/2476876
An efficient synthesis of 2- or 4-iododibenzofurans through CuI-mediated sequential iodination/cycloetherification of two aromatic C–H bonds in <i>o</i>-arylphenols has been developed. Both the preexisting electron-withdrawing groups (NO<sub>2</sub>, 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.
2012-10-19 00:00:00
preexisting
Mechanistic StudiesAn
Sequential
DFT calculations
Mechanistic studies
cycloetherification
sequential
iodide
Iodination
CN
activation
CHO
Iododibenzofuran
dibenzofuran library synthesis
iodination
iododibenzofuran
Synthesi
Cu
bond