Iodocyclization of Ethoxyethyl Ethers to Alkynes: A Broadly Applicable Synthesis of 3-Iodobenzo[b]furans

Iodocyclization of Ethoxyethyl Ethers to Alkynes: A Broadly Applicable Synthesis of 3-Iodobenzo[b]furans

A wide variety of 3-iodobenzo[b]furans were readily prepared by iodocyclization of 2-alkynyl-1-(1-ethoxyethoxy)benzenes with the I(coll)2PF6−BF3·OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also...

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Veröffentlicht in:Organic letters 2008-11, Vol.10 (21), p.4967-4970
Hauptverfasser: Okitsu, Takashi, Nakazawa, Daisuke, Taniguchi, Rie, Wada, Akimori
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemical synthesis
Alkynes - chemistry
Cyanides - chemistry
Cyclization
Ethyl Ethers - chemistry
Furans - chemical synthesis
Furans - chemistry
Iodine - chemistry
Iodobenzenes - chemistry
Molecular Structure
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Zusammenfassung:A wide variety of 3-iodobenzo[b]furans were readily prepared by iodocyclization of 2-alkynyl-1-(1-ethoxyethoxy)benzenes with the I(coll)2PF6−BF3·OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also discussed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol8020463