Chemical Reviews, volume 109, issue 5, pages 2119-2183

C−F Bond Activation in Organic Synthesis

Hideki Amii ¹

Kenji UNEYAMA ¹

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Department of Chemistry, Graduate School of Science, Kobe University, Kobe 657-8501, Japan, and Department of Applied Chemistry, Faculty of Engineering, Okayama Univeristy, Okayama 700-8530, Japan

Kobe University

Okayama University

Publication type: Journal Article

Publication date: 2009-03-30

American Chemical Society (ACS)

Journal: Chemical Reviews

Quartile SCImago

Quartile WOS

Impact factor: 62.1

ISSN: 00092665, 15206890

DOI: 10.1021/cr800388c

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General Chemistry

Abstract

Fluorine has received great attention in all fields of science. “Small atom with a big ego” was the title of the Symposium at the ACS meeting in San Francisco in 2000, where a number of the current scientific and industrial aspects of fluorine chemistry made possible by the small size and high electronegativity of the atom were discussed. This small atom has provided mankind with significant benefits in special products such as poly(tetrafluroethylene) (PTFE), freon, fluoro-liquid crystals, optical fiber, pharmaceutical and agrochemical compounds, and so on, all of which have their own unique properties that are otherwise difficult to obtain.1 For instance, at present, up to 30% of agrochemicals and 10% of pharmaceuticals currently used contain fluorine atoms. Therefore, organic fluorine compounds have received a great deal of interest and attention from the scientists involved in diverse fields of science and technology. Now, not only C-F bond formation but also selective C-F bond activation have become current subjects of active investigation from the viewpoint of effective synthesis of fluoroorganic compounds. The former is highlighted by designing a sophisticated fluorinating reagent for regioand stereocontrolled fluorination and developing versatile multifunctional and easily prepared building blocks. C-F bond formation has been treated extensively in several reviews2 and books.3 The latter is a subject that has been less explored but would be promising for selective defluorination of aliphatic fluorides, cross-coupling with aryl fluorides, and * To whom correspondence should be addressed. Phone: 81-78-803-5799. Fax: 81-78-803-5799. E-mail: amii@kobe-u.ac.jp and uneyamak@cc.okayamau.ac.jp. † Kobe University. ‡ Okayama University. Chem. Rev. 2009, 109, 2119–2183 2119

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Top-30

Citations by journals

	20 40 60 80 100 120 140
Organic Letters	Organic Letters, 136, 10.18% Organic Letters 136 publications, 10.18%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 99, 7.41% Angewandte Chemie - International Edition 99 publications, 7.41%
Angewandte Chemie	Angewandte Chemie, 99, 7.41% Angewandte Chemie 99 publications, 7.41%
Organometallics	Organometallics, 62, 4.64% Organometallics 62 publications, 4.64%
Journal of the American Chemical Society	Journal of the American Chemical Society, 62, 4.64% Journal of the American Chemical Society 62 publications, 4.64%
Journal of Organic Chemistry	Journal of Organic Chemistry, 62, 4.64% Journal of Organic Chemistry 62 publications, 4.64%
Chemistry - A European Journal	Chemistry - A European Journal, 62, 4.64% Chemistry - A European Journal 62 publications, 4.64%
Journal of Fluorine Chemistry	Journal of Fluorine Chemistry, 58, 4.34% Journal of Fluorine Chemistry 58 publications, 4.34%
Chemical Communications	Chemical Communications, 52, 3.89% Chemical Communications 52 publications, 3.89%
ACS Catalysis	ACS Catalysis, 40, 2.99% ACS Catalysis 40 publications, 2.99%
Chemical Science	Chemical Science, 33, 2.47% Chemical Science 33 publications, 2.47%
Tetrahedron Letters	Tetrahedron Letters, 32, 2.4% Tetrahedron Letters 32 publications, 2.4%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 29, 2.17% Advanced Synthesis and Catalysis 29 publications, 2.17%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 29, 2.17% Organic Chemistry Frontiers 29 publications, 2.17%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 28, 2.1% Organic and Biomolecular Chemistry 28 publications, 2.1%
Dalton Transactions	Dalton Transactions, 27, 2.02% Dalton Transactions 27 publications, 2.02%
Tetrahedron	Tetrahedron, 22, 1.65% Tetrahedron 22 publications, 1.65%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 20, 1.5% European Journal of Organic Chemistry 20 publications, 1.5%
Synlett	Synlett, 16, 1.2% Synlett 16 publications, 1.2%
European Journal of Inorganic Chemistry	European Journal of Inorganic Chemistry, 15, 1.12% European Journal of Inorganic Chemistry 15 publications, 1.12%
RSC Advances	RSC Advances, 14, 1.05% RSC Advances 14 publications, 1.05%
Chemistry Letters	Chemistry Letters, 13, 0.97% Chemistry Letters 13 publications, 0.97%
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 11, 0.82% Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 11 publications, 0.82%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 10, 0.75% Chemistry - An Asian Journal 10 publications, 0.75%
Chemical Reviews	Chemical Reviews, 10, 0.75% Chemical Reviews 10 publications, 0.75%
Synthesis	Synthesis, 9, 0.67% Synthesis 9 publications, 0.67%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 9, 0.67% Asian Journal of Organic Chemistry 9 publications, 0.67%
Nature Communications	Nature Communications, 8, 0.6% Nature Communications 8 publications, 0.6%
ChemCatChem	ChemCatChem, 8, 0.6% ChemCatChem 8 publications, 0.6%
	20 40 60 80 100 120 140

Citations by publishers

	50 100 150 200 250 300 350 400 450
American Chemical Society (ACS)	American Chemical Society (ACS), 406, 30.39% American Chemical Society (ACS) 406 publications, 30.39%
Wiley	Wiley, 404, 30.24% Wiley 404 publications, 30.24%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 214, 16.02% Royal Society of Chemistry (RSC) 214 publications, 16.02%
Elsevier	Elsevier, 169, 12.65% Elsevier 169 publications, 12.65%
Springer Nature	Springer Nature, 34, 2.54% Springer Nature 34 publications, 2.54%
Thieme	Thieme, 25, 1.87% Thieme 25 publications, 1.87%
The Chemical Society of Japan	The Chemical Society of Japan, 18, 1.35% The Chemical Society of Japan 18 publications, 1.35%
Society of Synthetic Organic Chemistry	Society of Synthetic Organic Chemistry, 11, 0.82% Society of Synthetic Organic Chemistry 11 publications, 0.82%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 8, 0.6% Multidisciplinary Digital Publishing Institute (MDPI) 8 publications, 0.6%
Beilstein-Institut	Beilstein-Institut, 6, 0.45% Beilstein-Institut 6 publications, 0.45%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 4, 0.3% Shanghai Institute of Organic Chemistry 4 publications, 0.3%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 4, 0.3% American Association for the Advancement of Science (AAAS) 4 publications, 0.3%
Frontiers Media S.A.	Frontiers Media S.A., 3, 0.22% Frontiers Media S.A. 3 publications, 0.22%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 3, 0.22% The Japan Institute of Heterocyclic Chemistry 3 publications, 0.22%
CSIRO Publishing	CSIRO Publishing, 2, 0.15% CSIRO Publishing 2 publications, 0.15%
SAGE	SAGE, 2, 0.15% SAGE 2 publications, 0.15%
Pleiades Publishing	Pleiades Publishing, 2, 0.15% Pleiades Publishing 2 publications, 0.15%
Taylor & Francis	Taylor & Francis, 2, 0.15% Taylor & Francis 2 publications, 0.15%
Bentham Science	Bentham Science, 1, 0.07% Bentham Science 1 publication, 0.07%
International Union of Crystallography (IUCr)	International Union of Crystallography (IUCr), 1, 0.07% International Union of Crystallography (IUCr) 1 publication, 0.07%
Nonferrous Metals Society of China	Nonferrous Metals Society of China, 1, 0.07% Nonferrous Metals Society of China 1 publication, 0.07%
Akademiai Kiado	Akademiai Kiado, 1, 0.07% Akademiai Kiado 1 publication, 0.07%
KeAi Communications Co.	KeAi Communications Co., 1, 0.07% KeAi Communications Co. 1 publication, 0.07%
Social Science Electronic Publishing	Social Science Electronic Publishing, 1, 0.07% Social Science Electronic Publishing 1 publication, 0.07%
King Saud University	King Saud University, 1, 0.07% King Saud University 1 publication, 0.07%
World Scientific	World Scientific, 1, 0.07% World Scientific 1 publication, 0.07%
Scientific Research Publishing	Scientific Research Publishing, 1, 0.07% Scientific Research Publishing 1 publication, 0.07%
Japan Academy	Japan Academy, 1, 0.07% Japan Academy 1 publication, 0.07%
Japan Petroleum Institute	Japan Petroleum Institute, 1, 0.07% Japan Petroleum Institute 1 publication, 0.07%
	50 100 150 200 250 300 350 400 450

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Statistics recalculated weekly.

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Amii H., UNEYAMA K. C−F Bond Activation in Organic Synthesis // Chemical Reviews. 2009. Vol. 109. No. 5. pp. 2119-2183.

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Amii H., UNEYAMA K. C−F Bond Activation in Organic Synthesis // Chemical Reviews. 2009. Vol. 109. No. 5. pp. 2119-2183.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/cr800388c

UR - https://doi.org/10.1021/cr800388c

TI - C−F Bond Activation in Organic Synthesis

T2 - Chemical Reviews

AU - UNEYAMA, Kenji

AU - Amii, Hideki

PY - 2009

DA - 2009/03/30 00:00:00

PB - American Chemical Society (ACS)

SP - 2119-2183

IS - 5

VL - 109

SN - 0009-2665

SN - 1520-6890

ER -

BibTex |

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BibTex Copy

@article{2009_Amii,

author = {Kenji UNEYAMA and Hideki Amii},

title = {C−F Bond Activation in Organic Synthesis},

journal = {Chemical Reviews},

year = {2009},

volume = {109},

publisher = {American Chemical Society (ACS)},

month = {mar},

url = {https://doi.org/10.1021/cr800388c},

number = {5},

pages = {2119--2183},

doi = {10.1021/cr800388c}

}

MLA

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MLA Copy

Amii, Hideki, and Kenji UNEYAMA. “C−F Bond Activation in Organic Synthesis.” Chemical Reviews, vol. 109, no. 5, Mar. 2009, pp. 2119-2183. https://doi.org/10.1021/cr800388c.

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Publisher

American Chemical Society (ACS)

Journal

Chemical Reviews

Quartile SCImago

Quartile WOS

Impact factor

62.1

ISSN

00092665 (Print)
15206890 (Electronic)