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Iridium‐Catalyzed Intramolecular Methoxy C−H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3‐Substituted Benzofurans from o ‐Methoxyphenylalkynes
Author(s) -
Torigoe Takeru,
Ohmura Toshimichi,
Suginome Michinori
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602152
Subject(s) - intramolecular force , triple bond , iridium , catalysis , alkyne , chemistry , medicinal chemistry , toluene , carbon fibers , ether , double bond , organic chemistry , materials science , composite number , composite material
Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C−H bond of a methoxy group in 1‐methoxy‐2‐(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p ‐xylene at 135 °C in the presence of an iridium catalyst. The initial 5‐exo cyclization products underwent double‐bond migration during the reaction to give 3‐(arylmethyl)benzofurans in high yields.