A Catalytic Reaction of Alkynes via Multiple-Site Functionalization

Subramanian Karur; S. R.S.Saibabu Kotti; Xin Xu; John F. Cannon; Allan Headley; Guigen Li

doi:10.1021/ja0304188

A Catalytic Reaction of Alkynes via Multiple-Site Functionalization

Subramanian Karur, S. R.S.Saibabu Kotti, Xin Xu, John F. Cannon, Allan Headley, Guigen Li

Chemistry and Biochemistry

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

32 Scopus citations

Abstract

The first multiple-site activation of alkynes with amine/halogen functionalities has been established. The reaction was performed by treating alkyne with N,N-dichlorobenzenesulfonamide at 80 °C in the presence of palladium acetate catalyst. A new mechanism was proposed which involves the novel formation of β-halovinyl palladium and π-allylpalladium species. Excellent regio- and stereoselectivities were achieved with the absolute structure determined by X-ray structural analysis.

Original language	English
Pages (from-to)	13340-13341
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	44
DOIs	https://doi.org/10.1021/ja0304188
State	Published - Nov 5 2003

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abstract = "The first multiple-site activation of alkynes with amine/halogen functionalities has been established. The reaction was performed by treating alkyne with N,N-dichlorobenzenesulfonamide at 80 °C in the presence of palladium acetate catalyst. A new mechanism was proposed which involves the novel formation of β-halovinyl palladium and π-allylpalladium species. Excellent regio- and stereoselectivities were achieved with the absolute structure determined by X-ray structural analysis.",

author = "Subramanian Karur and Kotti, {S. R.S.Saibabu} and Xin Xu and Cannon, {John F.} and Allan Headley and Guigen Li",

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AU - Karur, Subramanian

AU - Kotti, S. R.S.Saibabu

AU - Xu, Xin

AU - Cannon, John F.

AU - Headley, Allan

AU - Li, Guigen

PY - 2003/11/5

Y1 - 2003/11/5

N2 - The first multiple-site activation of alkynes with amine/halogen functionalities has been established. The reaction was performed by treating alkyne with N,N-dichlorobenzenesulfonamide at 80 °C in the presence of palladium acetate catalyst. A new mechanism was proposed which involves the novel formation of β-halovinyl palladium and π-allylpalladium species. Excellent regio- and stereoselectivities were achieved with the absolute structure determined by X-ray structural analysis.

AB - The first multiple-site activation of alkynes with amine/halogen functionalities has been established. The reaction was performed by treating alkyne with N,N-dichlorobenzenesulfonamide at 80 °C in the presence of palladium acetate catalyst. A new mechanism was proposed which involves the novel formation of β-halovinyl palladium and π-allylpalladium species. Excellent regio- and stereoselectivities were achieved with the absolute structure determined by X-ray structural analysis.

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JF - Journal of the American Chemical Society

IS - 44

ER -

A Catalytic Reaction of Alkynes via Multiple-Site Functionalization

Abstract

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