Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Vanessa Kar Yan Lo; Karen Ka Yan Kung; Man Kin Wong; Chi Ming Che

doi:10.1016/j.jorganchem.2008.12.008

Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Vanessa Kar Yan Lo, Karen Ka Yan Kung, Man Kin Wong, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

125 Citations (Scopus)

Abstract

Propargylamines are synthesized in high yields via a gold(III) (C^N) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 °C. Excellent diastereoselectivities (up to 99:1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au(C^N)Cl2] complex (N^CH = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812.

Original language	English
Pages (from-to)	583-591
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	694
Issue number	4
DOIs	https://doi.org/10.1016/j.jorganchem.2008.12.008
Publication status	Published - 15 Feb 2009

Keywords

Gold(III) catalyst
Prolinol derivatives
Propargylamines
Three-component coupling reaction

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

More information

10.1016/j.jorganchem.2008.12.008

Cite this

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title = "Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes",

abstract = "Propargylamines are synthesized in high yields via a gold(III) (C^N) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 °C. Excellent diastereoselectivities (up to 99:1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au(C^N)Cl2] complex (N^CH = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812.",

keywords = "Gold(III) catalyst, Prolinol derivatives, Propargylamines, Three-component coupling reaction",

author = "Lo, {Vanessa Kar Yan} and Kung, {Karen Ka Yan} and Wong, {Man Kin} and Che, {Chi Ming}",

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doi = "10.1016/j.jorganchem.2008.12.008",

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Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes. / Lo, Vanessa Kar Yan; Kung, Karen Ka Yan; Wong, Man Kin et al.
In: Journal of Organometallic Chemistry, Vol. 694, No. 4, 15.02.2009, p. 583-591.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

AU - Lo, Vanessa Kar Yan

AU - Kung, Karen Ka Yan

AU - Wong, Man Kin

AU - Che, Chi Ming

PY - 2009/2/15

Y1 - 2009/2/15

N2 - Propargylamines are synthesized in high yields via a gold(III) (C^N) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 °C. Excellent diastereoselectivities (up to 99:1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au(C^N)Cl2] complex (N^CH = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812.

AB - Propargylamines are synthesized in high yields via a gold(III) (C^N) complex-catalyzed three-component coupling reaction of aldehydes, amines and alkynes in water at 40 °C. Excellent diastereoselectivities (up to 99:1) have been achieved when chiral prolinol derivatives are employed as the amine component. Notably, the [Au(C^N)Cl2] complex (N^CH = 2-phenylpyridine) could be repeatedly used for 10 reaction cycles, leading to an overall turnover number of 812.

KW - Gold(III) catalyst

KW - Prolinol derivatives

KW - Propargylamines

KW - Three-component coupling reaction

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U2 - 10.1016/j.jorganchem.2008.12.008

DO - 10.1016/j.jorganchem.2008.12.008

M3 - Journal article

SN - 0022-328X

VL - 694

SP - 583

EP - 591

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 4

ER -

Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Abstract

Keywords

ASJC Scopus subject areas

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