Intramolecular cyclization of phenol derivatives with CC double bond in a side chain |
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Institution: | Department of Molecular Science and Technology, Faculty of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan;Research Center for Materials Science, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8602 Japan |
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Abstract: | Intramolecular cyclization of phenol derivatives with C C double bond on a side chain was examined using copper and silver catalyst. For example, 2-allylphenol (1a) was converted to 2,3-dihydro-2-methylbenzofuran (2a) in 70% yield using Cu(OTf)2 or in 90% yield using AgClO4. This catalysis was applied to cyclization of 2-allylphenol derivatives, 2-(3-butenyl)phenol, benzoic acids with C C double bond, 2-allyl-N-tosylaniline, and 2-(3-butenyloxy)phenol. Furthermore, allyl phenyl ether was converted to 2a via Claisen rearrangement and cyclization. |
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