Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

S. R.S.Saibabu Kotti; Xin Xu; Yining Wang; Allan D. Headley; Guigen Li

doi:10.1016/j.tetlet.2004.08.040

Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

S. R.S.Saibabu Kotti, Xin Xu, Yining Wang, Allan D. Headley, Guigen Li

Chemistry and Biochemistry

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

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Abstract

The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl ₂ proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol %). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples.

Original language	English
Pages (from-to)	7209-7212
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2004.08.040
State	Published - Sep 20 2004

Keywords

Aminohalogenation
Cinnamates
Copper(I)triflate
Ionic liquid

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10.1016/j.tetlet.2004.08.040

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title = "Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters",

abstract = "The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl 2 proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol %). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples.",

keywords = "Aminohalogenation, Cinnamates, Copper(I)triflate, Ionic liquid",

author = "Kotti, {S. R.S.Saibabu} and Xin Xu and Yining Wang and Headley, {Allan D.} and Guigen Li",

note = "Funding Information: We gratefully acknowledge the National Institutes of Health (CA 99995-1, R15) and the Robert A. Welch Foundation (D-1361, D-1460) for the generous support of this work. We thank David Chen, Cody Timmons for their assistance. ",

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doi = "10.1016/j.tetlet.2004.08.040",

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T1 - Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

AU - Kotti, S. R.S.Saibabu

AU - Xu, Xin

AU - Wang, Yining

AU - Headley, Allan D.

AU - Li, Guigen

N1 - Funding Information: We gratefully acknowledge the National Institutes of Health (CA 99995-1, R15) and the Robert A. Welch Foundation (D-1361, D-1460) for the generous support of this work. We thank David Chen, Cody Timmons for their assistance.

PY - 2004/9/20

Y1 - 2004/9/20

N2 - The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl 2 proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol %). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples.

AB - The ionic liquid, butylmethylimidazolium tetrafluoroborate ([Bmim][BF4]), was found to be superior to classical organic solvents for the metal catalyzed regio- and stereoselective aminohalogenation of cinnamic esters. The aminohalogenation reaction of cinnamic esters with p-TsNCl 2 proceeded at a faster rate (within 12 h) in the presence of a reduced amount of catalyst (CuOTf, 6.0 mol %). Good yields (76-82%) and excellent regio- and stereoselectivity (one isomer) were achieved for eight examples.

KW - Aminohalogenation

KW - Cinnamates

KW - Copper(I)triflate

KW - Ionic liquid

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U2 - 10.1016/j.tetlet.2004.08.040

DO - 10.1016/j.tetlet.2004.08.040

M3 - Article

AN - SCOPUS:4444371658

SN - 0040-4039

VL - 45

SP - 7209

EP - 7212

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

Ionic liquid media resulted in more efficient regio- and stereoselective aminohalogenation of cinnamic esters

Abstract

Keywords

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