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Gold‐Catalyzed Carboalkoxylations of 2‐Ethynylbenzyl Ethers to form 1‐ and 2‐Indanones Chemoselectively: Effects of Ligands and Solvents
Author(s) -
Wang ChiouDong,
Hsieh YiFeng,
Liu RaiShung
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300988
Subject(s) - chemistry , nitromethane , phosphine , catalysis , biphenyl , mesitylene , medicinal chemistry , organic chemistry , toluene
The selective syntheses of 1‐ and 2‐indanone compounds from 2‐ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phosphine]gold hexafluoroantimonate [P(C 6 F 5 ) 3 AuSbF 6 ] in nitromethane (MeNO 2 ) preferably gives 1‐indanones whereas [( ortho ‐biphenyl)di( tert ‐butyl)phosphine]gold triflimide [P( t Bu) 2 ( o ‐biphenyl)AuNTf 2 ] in dichloroethane tends to form 2‐indanone derivatives. For 2‐indanone products, we isolated two indenyl methyl ethers for deuterium labeling analyses, providing evidence for π‐alkyne activation.