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CuI-Mediated Sequential Iodination/Cycloetherification of o-Arylphenols: Synthesis of 2- or 4-Iododibenzofurans and Mechanistic Studies.
MedLine Citation:
PMID:  23025569     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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:
Jiaji Zhao; Qi Zhang; Lanying Liu; Yimiao He; Jing Li; Juan Li; Qiang Zhu
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-2
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-2     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health , Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530, P. R. China, and Department of Chemistry, Jinan University , Huangpu Road West 601, Guangzhou 510632, P. R. China.
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