Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

Pierrick Nun; Ruben S. Ramon; Sylvain Gaillard; Steven P. Nolan

doi:10.1016/j.jorganchem.2010.08.052

Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

Pierrick Nun, Ruben S. Ramon, Sylvain Gaillard, Steven P. Nolan

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

Abstract

The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Bronsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes. (C) 2010 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	711
Number of pages	5
Journal	Journal of Organometallic Chemistry
Volume	696
Issue number	1
DOIs	https://doi.org/10.1016/j.jorganchem.2010.08.052
Publication status	Published - 1 Jan 2011

Keywords

Gold catalysis
Alkyne hydration
Acid activation
Ketones
GOLD(I) COMPLEXES
CYCLOISOMERIZATION
ACTIVATION
ACETALS
LIGAND

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10.1016/j.jorganchem.2010.08.052

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title = "Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading",

abstract = "The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Bronsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes. (C) 2010 Elsevier B.V. All rights reserved.",

keywords = "Gold catalysis, Alkyne hydration, Acid activation, Ketones, GOLD(I) COMPLEXES, CYCLOISOMERIZATION, ACTIVATION, ACETALS, LIGAND",

author = "Pierrick Nun and Ramon, \{Ruben S.\} and Sylvain Gaillard and Nolan, \{Steven P.\}",

year = "2011",

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doi = "10.1016/j.jorganchem.2010.08.052",

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pages = "711",

journal = "Journal of Organometallic Chemistry",

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T1 - Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

AU - Nun, Pierrick

AU - Ramon, Ruben S.

AU - Gaillard, Sylvain

AU - Nolan, Steven P.

PY - 2011/1/1

Y1 - 2011/1/1

N2 - The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Bronsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes. (C) 2010 Elsevier B.V. All rights reserved.

AB - The use of [(IPr)AuOH] as versatile, air- and moisture-stable pre-catalyst permits the in situ generation of the cationic gold(I) species [(IPr)Au]X after reaction with a Bronsted acid. This catalytic system presents as a main advantage the lack of use of a silver salt activator or co-catalyst which is often air-, light- and moisture-sensitive. A general gold(I)-catalyzed procedure using this in situ activation at very low catalyst loading is reported for the hydration of a broad range of internal and terminal alkynes. (C) 2010 Elsevier B.V. All rights reserved.

KW - Gold catalysis

KW - Alkyne hydration

KW - Acid activation

KW - Ketones

KW - GOLD(I) COMPLEXES

KW - CYCLOISOMERIZATION

KW - ACTIVATION

KW - ACETALS

KW - LIGAND

UR - https://www.scopus.com/pages/publications/78649840066

U2 - 10.1016/j.jorganchem.2010.08.052

DO - 10.1016/j.jorganchem.2010.08.052

M3 - Article

SN - 0022-328X

VL - 696

SP - 711

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1

ER -

Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

Abstract

Keywords

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Molecular assembly using gold catalysis: Molecular assembly using gold catalysis

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Efficient silver-free gold(I)-catalyzed hydration of alkynes at low catalyst loading

Abstract

Keywords

Access to Document

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Projects

Molecular assembly using gold catalysis: Molecular assembly using gold catalysis

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