Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source

Jianlin Han; Yufeng Li; Sanjun Zhi; Yi Pan; Cody Timmons; Guigen Li

doi:10.1016/j.tetlet.2006.07.143

Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source

Jianlin Han, Yufeng Li, Sanjun Zhi, Yi Pan, Cody Timmons, Guigen Li

Chemistry and Biochemistry

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

45 Scopus citations

Abstract

N,N-Dichloro-p-toluenesulfonamide (TsNCl₂) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl₂ to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient α,β-unsaturated alkenes.

Original language	English
Pages (from-to)	7225-7228
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2006.07.143
State	Published - Oct 2 2006

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title = "Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source",

abstract = "N,N-Dichloro-p-toluenesulfonamide (TsNCl2) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl2 to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient α,β-unsaturated alkenes.",

author = "Jianlin Han and Yufeng Li and Sanjun Zhi and Yi Pan and Cody Timmons and Guigen Li",

note = "Funding Information: We gratefully acknowledge the 863 High Technology Program (PR China) and Welch Foundation (D-1361, USA) for the generous financial support. The research funds for Y.P. from Qing-Lan program of Jiangsu Province and Kua-Shi-Ji program of Education Ministry of China are also acknowledged. ",

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doi = "10.1016/j.tetlet.2006.07.143",

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T1 - Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source

AU - Han, Jianlin

AU - Li, Yufeng

AU - Zhi, Sanjun

AU - Pan, Yi

AU - Timmons, Cody

AU - Li, Guigen

N1 - Funding Information: We gratefully acknowledge the 863 High Technology Program (PR China) and Welch Foundation (D-1361, USA) for the generous financial support. The research funds for Y.P. from Qing-Lan program of Jiangsu Province and Kua-Shi-Ji program of Education Ministry of China are also acknowledged.

PY - 2006/10/2

Y1 - 2006/10/2

N2 - N,N-Dichloro-p-toluenesulfonamide (TsNCl2) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl2 to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient α,β-unsaturated alkenes.

AB - N,N-Dichloro-p-toluenesulfonamide (TsNCl2) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl2 to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient α,β-unsaturated alkenes.

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U2 - 10.1016/j.tetlet.2006.07.143

DO - 10.1016/j.tetlet.2006.07.143

M3 - Article

AN - SCOPUS:33748793089

SN - 0040-4039

VL - 47

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source

Abstract

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