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

Organic letters (2012-10-03)
Jiaji Zhao, Qi Zhang, Lanying Liu, Yimiao He, Jing Li, Juan Li, Qiang Zhu
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.

MATERIALS
Product Number
Brand
Product Description

Supelco
Dibenzofuran, analytical standard
Supelco
Diethyl ether, analytical standard
Dibenzo[b,d]furan, BCR®, certified reference material
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%
Sigma-Aldrich
Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%
Sigma-Aldrich
Dibenzofuran, 98%
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Copper(I) iodide, 99.999% trace metals basis
Sigma-Aldrich
Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor
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Diethyl ether, contains BHT as inhibitor, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8%
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Diethyl ether, puriss., contains ~5 mg/L 2,6-di-tert.-butyl-4-methylphenol as stabilizer, meets analytical specification of Ph. Eur., BP, ≥99.5% (GC)
Sigma-Aldrich
Diethyl ether, reagent grade, ≥98%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor
Sigma-Aldrich
Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor
Sigma-Aldrich
Diethyl ether, suitable for HPLC, ≥99.9%, inhibitor-free
Sigma-Aldrich
Diethyl ether, ACS reagent, ≥98.0%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor
Sigma-Aldrich
Copper(I) iodide, 98%
Supelco
Ethyl ether solution, certified reference material, 2000 μg/mL in methanol