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Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents
Journal article   Peer reviewed

Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 2-indanones chemoselectively: Effects of ligands and solvents

Chiou-Dong Wang, Yi-Feng Hsieh and Rai-Shung Liu
Advanced Synthesis and Catalysis, Vol.356(1), pp.144-152
13/01/2014

Abstract

1-indanones 2-ethynylbenzyl ethers 2-indanones Carboalkoxylations Gold catalysis
The selective syntheses of 1- and 2-indan-one compounds from 2-ethynylbenzyl ethers have been achieved with suitable catalysts and solvents. The highly acidic [tris(pentafluorophenyl)phos-phine]gold hexafluoroantimonate [(C <sub>6</sub> F <sub>5</sub> ) <sub>3</sub> AuSbF <sub>6</sub> ] in nitromethane (MeNO <sub>2</sub> ) preferably gives 1-indan-ones whereas [(ortho-biphenyl) di(tert-butyl)phosphine] gold triflimide [(tBu) <sub>2</sub> (o-biphenyl) AuNTf <sub>2</sub> ] 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 p-alkyne activation. © 2014 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.

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