Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

Pratik P. Goswami; Victoria P. Suding; Angela S. Carlson; Joseph J. Topczewski

doi:10.1002/ejoc.201600856

Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

Pratik P. Goswami, Victoria P. Suding, Angela S. Carlson, Joseph J. Topczewski

Chemistry (Twin Cities)

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

17 Scopus citations

Abstract

This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.

Original language	English (US)
Pages (from-to)	4805-4809
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	28
DOIs	https://doi.org/10.1002/ejoc.201600856
State	Published - Oct 2016

Bibliographical note

Funding Information:
We thank Amy Ott for acquiring mass spectra. The American Chemical Society – Petroleum Research Fund (ACS-PRF) (PRF#56505-DNI1) and the University of Minnesota are thanked for financial support. V. P. S. acknowledges the University of Minnesota – Undergraduate Research Opportunity (UMN-UROP) for support.

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Amines
Azides
Click chemistry
Green chemistry

Publisher link

10.1002/ejoc.201600856

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title = "Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution",

abstract = "This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.",

keywords = "Amines, Azides, Click chemistry, Green chemistry",

author = "Goswami, {Pratik P.} and Suding, {Victoria P.} and Carlson, {Angela S.} and Topczewski, {Joseph J.}",

note = "Funding Information: We thank Amy Ott for acquiring mass spectra. The American Chemical Society – Petroleum Research Fund (ACS-PRF) (PRF#56505-DNI1) and the University of Minnesota are thanked for financial support. V. P. S. acknowledges the University of Minnesota – Undergraduate Research Opportunity (UMN-UROP) for support. Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

month = oct,

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AU - Goswami, Pratik P.

AU - Suding, Victoria P.

AU - Carlson, Angela S.

AU - Topczewski, Joseph J.

N1 - Funding Information: We thank Amy Ott for acquiring mass spectra. The American Chemical Society – Petroleum Research Fund (ACS-PRF) (PRF#56505-DNI1) and the University of Minnesota are thanked for financial support. V. P. S. acknowledges the University of Minnesota – Undergraduate Research Opportunity (UMN-UROP) for support. Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/10

Y1 - 2016/10

N2 - This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.

AB - This report describes the direct conversion of aldehydes and ketones into alkyl azides by the addition of common organometallic reagents and tandem conversion of the resulting alkoxides without isolation of the intermediate alcohols. A wide range of aldehydes and organometallic reagents (R–Li or R–MgX) are suitable participants in this process. Additional reaction telescoping beyond azide formation is demonstrated.

KW - Amines

KW - Azides

KW - Click chemistry

KW - Green chemistry

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Direct Conversion of Aldehydes and Ketones into Azides by Sequential Nucleophilic Addition and Substitution

Abstract

Bibliographical note

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