Journal of the American Chemical Society, volume 137, issue 31, pages 9820-9823

Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution

Chao Liu ¹

Xiaoqing Wang ¹

Zhaodong Li ¹

Lei Cui ¹

Chaozhong Li ^{1, 2}

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Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China |

School of Chemical Engineering, Ningbo University of Technology, No. 89 Cuibai Road, Ningbo 315016, P. R. China |

Publication type: Journal Article

Publication date: 2015-07-30

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/jacs.5b06821

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General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH3CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific azidation.

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Canadian Journal of Chemistry	Canadian Journal of Chemistry, 1, 0.6% Canadian Journal of Chemistry 1 publication, 0.6%
JACS Au	JACS Au, 1, 0.6% JACS Au 1 publication, 0.6%
Catalysts	Catalysts, 1, 0.6% Catalysts 1 publication, 0.6%
Science China Chemistry	Science China Chemistry, 1, 0.6% Science China Chemistry 1 publication, 0.6%
Polymer	Polymer, 1, 0.6% Polymer 1 publication, 0.6%
Chem Catalysis	Chem Catalysis, 1, 0.6% Chem Catalysis 1 publication, 0.6%
	5 10 15 20 25 30

Citations by publishers

	10 20 30 40 50 60 70
American Chemical Society (ACS)	American Chemical Society (ACS), 67, 40.36% American Chemical Society (ACS) 67 publications, 40.36%
Wiley	Wiley, 41, 24.7% Wiley 41 publications, 24.7%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 34, 20.48% Royal Society of Chemistry (RSC) 34 publications, 20.48%
Elsevier	Elsevier, 6, 3.61% Elsevier 6 publications, 3.61%
Springer Nature	Springer Nature, 5, 3.01% Springer Nature 5 publications, 3.01%
Thieme	Thieme, 5, 3.01% Thieme 5 publications, 3.01%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 3, 1.81% Multidisciplinary Digital Publishing Institute (MDPI) 3 publications, 1.81%
Beilstein-Institut	Beilstein-Institut, 1, 0.6% Beilstein-Institut 1 publication, 0.6%
Canadian Science Publishing	Canadian Science Publishing, 1, 0.6% Canadian Science Publishing 1 publication, 0.6%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 1, 0.6% American Association for the Advancement of Science (AAAS) 1 publication, 0.6%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.6% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.6%
	10 20 30 40 50 60 70

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Liu C. et al. Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution // Journal of the American Chemical Society. 2015. Vol. 137. No. 31. pp. 9820-9823.

GOST all authors (up to 50) Copy

Liu C., Wang X., Li Z., Cui L., Li C. Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution // Journal of the American Chemical Society. 2015. Vol. 137. No. 31. pp. 9820-9823.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/jacs.5b06821

UR - https://doi.org/10.1021/jacs.5b06821

TI - Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution

T2 - Journal of the American Chemical Society

AU - Wang, Xiaoqing

AU - Li, Zhaodong

AU - Cui, Lei

AU - Li, Chaozhong

AU - Liu, Chao

PY - 2015

DA - 2015/07/30 00:00:00

PB - American Chemical Society (ACS)

SP - 9820-9823

IS - 31

VL - 137

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

Cite this

BibTex Copy

@article{2015_Liu,

author = {Xiaoqing Wang and Zhaodong Li and Lei Cui and Chaozhong Li and Chao Liu},

title = {Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution},

journal = {Journal of the American Chemical Society},

year = {2015},

volume = {137},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://doi.org/10.1021/jacs.5b06821},

number = {31},

pages = {9820--9823},

doi = {10.1021/jacs.5b06821}

}

MLA

Cite this

MLA Copy

Liu, Chao, et al. “Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution.” Journal of the American Chemical Society, vol. 137, no. 31, Jul. 2015, pp. 9820-9823. https://doi.org/10.1021/jacs.5b06821.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor

ISSN

00027863 (Print)
15205126 (Electronic)