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 x OEt2 combination. Aryl-, vinylic-, and alkyl-substituted alkynes undergo iodocyclization in good to excellent yields. The mechanism of the reaction is also discussed.
Okitsu
Takashi
T
Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan.
Nakazawa
Daisuke
D
Taniguchi
Rie
R
Wada
Akimori
A
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D005019:Ethyl Ethers / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure
D000480:Alkynes; D003486:Cyanides; D005019:Ethyl Ethers; D005663:Furans; D007462:Iodobenzenes; D007455:Iodine; C031905:iodobenzene; C039281:furan