Chemical Communications

, volume 55 , issue 51 , pages 7331-7334

Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature

Qi Miao ^{1, 2, 3, 4, 5, 6}

Shao Zhong ^{1, 2, 3, 4, 5, 6}

Cuiying Shi ^{1, 2, 3, 4, 5, 6}

Lifang Ma ^{1, 2, 3, 4, 5, 6}

Fang Wang ¹

Ruoqi Fu ^{1, 2, 3, 4, 5, 6}

Haochen Gao ^{1, 2, 3, 4, 5, 6}

Ziyuan Li ^{1, 2, 3, 4, 5, 6}

Hide authors affiliations Show authors affiliations: 6 affiliations

Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, China |

Department of Pharmaceutical and Biological Engineering

School of Chemical Engineering

⁴

SICHUAN University |

⁵

Chengdu 610065 |

⁶

CHINA |

Publication type: Journal Article

Publication date: 2019-05-29

Royal Society of Chemistry (RSC)

Chemical Communications

scimago Q1

wos Q2

SJR: 1.037

CiteScore: 7.4

Impact factor: 4.2

ISSN: 13597345, 1364548X

DOI: 10.1039/c9cc02739d

Copy DOI

PubMed ID: 31169286

Materials Chemistry

Metals and Alloys

Surfaces, Coatings and Films

General Chemistry

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Catalysis

Abstract

A TEMPO-catalysed direct amination of arene through C–H bond cleavage employing N-fluorobenzenesulfonimide (NFSI) as the amination reagent in good to excellent yields with broad arene scope in the absence of any metal, ligand or additive is reported. Unlike previous transition metal-catalysed aminations in which high reaction temperatures are usually necessary, this novel reaction at room temperature is the first example of C–H amination with NFSI that is realised via organocatalysis. The probable mechanism of this concise amination is also proposed.

Found

1 citation

Beloglazkina Elena

DSc in Chemistry, professor

296 publications, 3 248 citations, 11 reviews

h-index: 29

Lomonosov Moscow State University

1 citation

Luponosov Yuriy

🥼 🤝

DSc in Chemistry

113 publications, 2 526 citations, 13 reviews

h-index: 27

Enikolopov Institute of Synthetic Polymeric Materials of the Russian Academy of Sciences

1 citation

Vil' Vera

PhD in Chemistry

86 publications, 1 967 citations, 3 reviews

h-index: 24

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Yaremenko Ivan

PhD in Chemistry

60 publications, 1 567 citations, 5 reviews

h-index: 24

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Organic Chemistry

1 citation

Gorbunova Yuliya

DSc in Chemistry, professor, full member of the Russian Academy of Sciences

284 publications, 4 398 citations, 65 reviews

h-index: 34

Lomonosov Moscow State University

Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Lanthanides

Supramolecular chemistry

Tetrapyrrolic compounds

1 citation

Volcho Konstantin

DSc in Chemistry, professor of the Russian Academy of Sciences

279 publications, 3 898 citations, 65 reviews

h-index: 31

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Danilkina Natalia

44 publications, 625 citations

h-index: 14

Saint Petersburg State University

Research interests

Bioorganic chemistry

Click chemistry

Heterocyclic compounds

Medicinal Chemistry

Organic Chemistry

1 citation

Osipov Sergey

DSc in Chemistry

138 publications, 2 739 citations, 3 reviews

h-index: 29

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

1 citation

Gazizov Almir

🥼

DSc in Chemistry

157 publications, 889 citations, 23 reviews

h-index: 14

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Heterocyclic compounds

Organic Chemistry

Organophosphorus chemistry

1 citation

Karasik Andrey

DSc in Chemistry, professor, associate member of the Russian Academy of Sciences

224 publications, 2 599 citations

h-index: 26

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Coordination Chemistry

Luminescence

Phosphorus ligands

1 citation

Dotsenko Viktor

DSc in Chemistry, professor

244 publications, 2 741 citations, 2 reviews

h-index: 22

North Caucasus Federal University

Kuban State University

Research interests

Active methylene compounds

Biological activity

Heterocyclic compounds

Malononitrile

Selenoamides

Thioamides

1 citation

Zagidullin Almaz

🥼 🤝

PhD in Chemistry

81 publications, 884 citations

h-index: 17

A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials

Coordination chemistry of phosphorus

Organoelement chemistry

Organophosphorus chemistry

Synthesis of chiral phosphorus-containing ligands

1 citation

Aksenov Aleksandr

🥼 🤝

DSc in Chemistry, professor

243 publications, 2 187 citations, 15 reviews

h-index: 24

North Caucasus Federal University

Research interests

Medicinal Chemistry

Organic Chemistry

1 citation

Sosnovskikh Vyacheslav

DSc in Chemistry, professor

355 publications, 4 721 citations

h-index: 30

Ural Federal University

1 citation

Ilkin Vladimir

PhD in Chemistry

16 publications, 187 citations

h-index: 7

Ural Federal University

Research interests

Catalysis

Heterocyclic compounds

Organic Chemistry

Synthetic Organic Chemistry

1 citation

Krylov Igor

PhD in Chemistry

78 publications, 1 885 citations, 18 reviews

h-index: 25

N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences

Research interests

Green chemistry

Organic Chemistry

Organic electrochemistry

Organic synthesis

Photochemistry

Plant protection

1 citation

Tikhomirov Alexander

🥼 🤝

DSc in Chemistry, associate professor

59 publications, 920 citations

h-index: 17

Mendeleev University of Chemical Technology of Russia

Gause Institute of New Antibiotics

Research interests

Medicinal Chemistry

1 citation

Ivanov Andrey

54 publications, 534 citations

h-index: 12

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

1 citation

Buev Evgeny

PhD in Chemistry

31 publications, 346 citations, 2 reviews

h-index: 9

Ural Federal University

Research interests

Chemistry of nitrogen-containing heterocycles

Organic Chemistry

Organic synthesis

Top-30

Journals

	1 2 3 4 5 6
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 6, 17.14% Organic Chemistry Frontiers 6 publications, 17.14%
Organic Letters	Organic Letters, 4, 11.43% Organic Letters 4 publications, 11.43%
RSC Advances	RSC Advances, 3, 8.57% RSC Advances 3 publications, 8.57%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 5.71% Advanced Synthesis and Catalysis 2 publications, 5.71%
Journal of Organic Chemistry	Journal of Organic Chemistry, 2, 5.71% Journal of Organic Chemistry 2 publications, 5.71%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 2, 5.71% Organic and Biomolecular Chemistry 2 publications, 5.71%
Transactions of Tianjin University	Transactions of Tianjin University, 1, 2.86% Transactions of Tianjin University 1 publication, 2.86%
Tetrahedron	Tetrahedron, 1, 2.86% Tetrahedron 1 publication, 2.86%
Chemical Record	Chemical Record, 1, 2.86% Chemical Record 1 publication, 2.86%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 2.86% Asian Journal of Organic Chemistry 1 publication, 2.86%
ACS Catalysis	ACS Catalysis, 1, 2.86% ACS Catalysis 1 publication, 2.86%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 2.86% Journal of the American Chemical Society 1 publication, 2.86%
Heterocycles	Heterocycles, 1, 2.86% Heterocycles 1 publication, 2.86%
Chemical Communications	Chemical Communications, 1, 2.86% Chemical Communications 1 publication, 2.86%
Chemical Reviews	Chemical Reviews, 1, 2.86% Chemical Reviews 1 publication, 2.86%
Electrochimica Acta	Electrochimica Acta, 1, 2.86% Electrochimica Acta 1 publication, 2.86%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 2.86% Russian Chemical Reviews 1 publication, 2.86%
ChemPlusChem	ChemPlusChem, 1, 2.86% ChemPlusChem 1 publication, 2.86%
Springer Proceedings in Materials	Springer Proceedings in Materials, 1, 2.86% Springer Proceedings in Materials 1 publication, 2.86%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.86% European Journal of Organic Chemistry 1 publication, 2.86%
Angewandte Chemie	Angewandte Chemie, 1, 2.86% Angewandte Chemie 1 publication, 2.86%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 1, 2.86% Angewandte Chemie - International Edition 1 publication, 2.86%
	1 2 3 4 5 6

Publishers

	2 4 6 8 10 12
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 12, 34.29% Royal Society of Chemistry (RSC) 12 publications, 34.29%
American Chemical Society (ACS)	American Chemical Society (ACS), 9, 25.71% American Chemical Society (ACS) 9 publications, 25.71%
Wiley	Wiley, 8, 22.86% Wiley 8 publications, 22.86%
Springer Nature	Springer Nature, 2, 5.71% Springer Nature 2 publications, 5.71%
Elsevier	Elsevier, 2, 5.71% Elsevier 2 publications, 5.71%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 1, 2.86% The Japan Institute of Heterocyclic Chemistry 1 publication, 2.86%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 2.86% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 2.86%
	2 4 6 8 10 12

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Miao Q. et al. Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature // Chemical Communications. 2019. Vol. 55. No. 51. pp. 7331-7334.

GOST all authors (up to 50) Copy

Miao Q., Zhong S., Shi C., Ma L., Wang F., Fu R., Gao H., Li Z. Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature // Chemical Communications. 2019. Vol. 55. No. 51. pp. 7331-7334.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1039/c9cc02739d

UR - https://xlink.rsc.org/?DOI=C9CC02739D

TI - Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature

T2 - Chemical Communications

AU - Miao, Qi

AU - Zhong, Shao

AU - Shi, Cuiying

AU - Ma, Lifang

AU - Wang, Fang

AU - Fu, Ruoqi

AU - Gao, Haochen

AU - Li, Ziyuan

PY - 2019

DA - 2019/05/29

PB - Royal Society of Chemistry (RSC)

SP - 7331-7334

IS - 51

VL - 55

PMID - 31169286

SN - 1359-7345

SN - 1364-548X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Miao,

author = {Qi Miao and Shao Zhong and Cuiying Shi and Lifang Ma and Fang Wang and Ruoqi Fu and Haochen Gao and Ziyuan Li},

title = {Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature},

journal = {Chemical Communications},

year = {2019},

volume = {55},

publisher = {Royal Society of Chemistry (RSC)},

month = {may},

url = {https://xlink.rsc.org/?DOI=C9CC02739D},

number = {51},

pages = {7331--7334},

doi = {10.1039/c9cc02739d}

}

MLA

Cite this

MLA Copy

Miao, Qi, et al. “Metal-free C–H amination of arene with N-fluorobenzenesulfonimide catalysed by nitroxyl radicals at room temperature.” Chemical Communications, vol. 55, no. 51, May. 2019, pp. 7331-7334. https://xlink.rsc.org/?DOI=C9CC02739D.

Publisher

Royal Society of Chemistry (RSC)

Journal

Chemical Communications

scimago Q1

wos Q2

SJR

1.037

CiteScore

7.4

Impact factor

4.2

ISSN

13597345 (Print)

1364548X (Electronic)