Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides

Prathima Surabhi; Xinghua Wu; Longqin Hu

doi:10.1016/j.tetlet.2006.04.144

Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides

Prathima Surabhi, Xinghua Wu, Longqin Hu

Ernest Mario School of Pharmacy, Medicinal Chemistry

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

14 Scopus citations

Abstract

Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily at room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields with electron-rich azides.

Original language	English (US)
Pages (from-to)	4609-4613
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.144
State	Published - Jul 3 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.04.144

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title = "Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides",

abstract = "Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily at room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields with electron-rich azides.",

author = "Prathima Surabhi and Xinghua Wu and Longqin Hu",

note = "Funding Information: We gratefully acknowledge the financial support of a research grant from the State of New Jersey Commission on Cancer Research and a research scholar grant from the American Cancer Society (to L.H.). We thank Professors Lawrence Williams and Spencer Knapp for helpful discussions. ",

year = "2006",

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doi = "10.1016/j.tetlet.2006.04.144",

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T1 - Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides

AU - Surabhi, Prathima

AU - Wu, Xinghua

AU - Hu, Longqin

N1 - Funding Information: We gratefully acknowledge the financial support of a research grant from the State of New Jersey Commission on Cancer Research and a research scholar grant from the American Cancer Society (to L.H.). We thank Professors Lawrence Williams and Spencer Knapp for helpful discussions.

PY - 2006/7/3

Y1 - 2006/7/3

N2 - Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily at room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields with electron-rich azides.

AB - Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily at room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields with electron-rich azides.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides

Abstract

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