Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes

Richard Marinus Petrus Veenboer; Stephanie Dupuy; Steven Patrick Nolan

doi:10.1021/cs501976s

Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes

Richard Marinus Petrus Veenboer, Stephanie Dupuy, Steven Patrick Nolan

Research output: Contribution to journal › Article › peer-review

Abstract

We report the use of cationic gold complexes [Au(NHC)(CH₃CN)][BF₄] and [{Au(NHC)}₂(μ-OH)][BF₄] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h^-1).

Original language	English
Pages (from-to)	1330-1334
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	2
Early online date	21 Jan 2015
DOIs	https://doi.org/10.1021/cs501976s
Publication status	Published - 6 Feb 2015

Keywords

Gold
Hydroalkoxylation
Alkynes
Vinyl ethers
Solvent-free

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10.1021/cs501976s

Nolan_2015_ACSC_Stereo_AM
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © 2015 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: http://dx.doi.org/10.1021/cs501976s
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title = "Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes",

abstract = "We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(μ-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h-1).",

keywords = "Gold, Hydroalkoxylation, Alkynes, Vinyl ethers, Solvent-free",

author = "Veenboer, {Richard Marinus Petrus} and Stephanie Dupuy and Nolan, {Steven Patrick}",

note = "The EPSRC and ERC are gratefully acknowledged for support.",

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T1 - Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes

AU - Veenboer, Richard Marinus Petrus

AU - Dupuy, Stephanie

AU - Nolan, Steven Patrick

N1 - The EPSRC and ERC are gratefully acknowledged for support.

PY - 2015/2/6

Y1 - 2015/2/6

N2 - We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(μ-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h-1).

AB - We report the use of cationic gold complexes [Au(NHC)(CH3CN)][BF4] and [{Au(NHC)}2(μ-OH)][BF4] (NHC = N-heterocyclic carbene) as highly active catalysts in the solvent-free hydroalkoxylation of internal alkynes using primary and secondary alcohols. Using this simple protocol, a broad range of (Z)-vinyl ethers were obtained in excellent yields and high stereoselectivities. The methodology allows for the use of catalyst loadings as low as 200 ppm for the addition of primary alcohols to internal alkynes (TON = 35 000, TOF = 2188 h-1).

KW - Gold

KW - Hydroalkoxylation

KW - Alkynes

KW - Vinyl ethers

KW - Solvent-free

UR - http://pubs.acs.org/doi/suppl/10.1021/cs501976s

U2 - 10.1021/cs501976s

DO - 10.1021/cs501976s

M3 - Article

SN - 2155-5435

VL - 5

SP - 1330

EP - 1334

JO - ACS Catalysis

JF - ACS Catalysis

IS - 2

ER -

Stereoselective gold(I)-catalyzed intermolecular hydroalkoxlation of alkynes

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