Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

Robert S. Paton; Feliu Maseras

doi:10.1021/ol9004646

Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

Robert S. Paton, Feliu Maseras

Department of Chemistry

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Abstract

The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product. © 2009 American Chemical Society.

Original language	English
Pages (from-to)	2237-2240
Journal	Organic Letters
Volume	11
Issue number	11
DOIs	https://doi.org/10.1021/ol9004646
Publication status	Published - 4 Jun 2009

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title = "Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study",

abstract = "The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product. {\textcopyright} 2009 American Chemical Society.",

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N2 - The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product. © 2009 American Chemical Society.

AB - The mechanistic and regiochemical aspects in the Au(I)-catalyzed intermolecular hydroalkoxylation of allenes have been studied computationally. The most favorable pathway is nucleophilic attack of an Au(I)-coordinated allene, which occurs irreversibly. An Au(I)-catalyzed mechanism is proposed that allows the facile interconversion of regioisomeric allylic ether products. The regioisomers are connected via a stabilized diether intermediate with a C-Au σ-bond, which successfully explains the observed regioselectivity for the thermodynamic product. © 2009 American Chemical Society.

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DO - 10.1021/ol9004646

M3 - Article

VL - 11

SP - 2237

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Gold(I)-catalyzed intermolecular hydroalkoxylation of allenes: A DFT study

Abstract

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