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ACS Central Science, volume 2, issue 5, pages 281-292

Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities

John H Hartwig ^{1, 2}

Matthew A Larsen ^{1, 2}

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Department of Chemistry, University of California, Berkeley, California 94720, United States |

Division of Chemical Sciences, Lawrence Berkeley Laboratory, Berkeley, California 94720, United States |

Publication type: Journal Article

Publication date: 2016-05-02

American Chemical Society (ACS)

Journal: ACS Central Science

Quartile SCImago

Quartile WOS

Impact factor: 18.2

ISSN: 23747943, 23747951

DOI: 10.1021/acscentsci.6b00032

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PubMed ID: 27294201

General Chemistry

General Chemical Engineering

Abstract

The functionalization of C–H bonds has created new approaches to preparing organic molecules by enabling new strategic “disconnections” during the planning of a synthetic route. Such functionalizations also have created the ability to derivatize complex molecules by modifying one or more of the many C–H bonds. For these reasons, researchers are developing new types of functionalization reactions of C–H bonds and new applications of these processes. These C–H bond functionalization reactions can be divided into two general classes: those directed by coordination to an existing functional group prior to the cleavage of the C–H bond (directed) and those occurring without coordination prior to cleavage of the C–H bond (undirected). The undirected functionalizations of C–H bonds are much less common and more challenging to develop than the directed reactions. This outlook will focus on undirected C–H bond functionalization, as well as related reactions that occur by a noncovalent association of the catalyst prior to C–H bond cleavage. The inherent challenges of conducting undirected functionalizations of C–H bonds and the methods for undirected functionalization that are being developed will be presented, along with the factors that govern selectivity in these reactions. Finally, this outlook discusses future directions for research on undirected C–H functionalization, with an emphasis on the limitations that must be overcome if this type of methodology is to become widely used in academia and in industry.

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	10 20 30 40 50 60
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 59, 9.12% Angewandte Chemie - International Edition 59 publications, 9.12%
Angewandte Chemie	Angewandte Chemie, 59, 9.12% Angewandte Chemie 59 publications, 9.12%
Journal of the American Chemical Society	Journal of the American Chemical Society, 50, 7.73% Journal of the American Chemical Society 50 publications, 7.73%
ACS Catalysis	ACS Catalysis, 44, 6.8% ACS Catalysis 44 publications, 6.8%
Organic Letters	Organic Letters, 28, 4.33% Organic Letters 28 publications, 4.33%
Chemistry - A European Journal	Chemistry - A European Journal, 27, 4.17% Chemistry - A European Journal 27 publications, 4.17%
Organometallics	Organometallics, 25, 3.86% Organometallics 25 publications, 3.86%
Chemical Communications	Chemical Communications, 20, 3.09% Chemical Communications 20 publications, 3.09%
Journal of Organic Chemistry	Journal of Organic Chemistry, 19, 2.94% Journal of Organic Chemistry 19 publications, 2.94%
Chemical Science	Chemical Science, 18, 2.78% Chemical Science 18 publications, 2.78%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 13, 2.01% Organic and Biomolecular Chemistry 13 publications, 2.01%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 13, 2.01% Organic Chemistry Frontiers 13 publications, 2.01%
Chemical Reviews	Chemical Reviews, 10, 1.55% Chemical Reviews 10 publications, 1.55%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 9, 1.39% European Journal of Organic Chemistry 9 publications, 1.39%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 9, 1.39% Asian Journal of Organic Chemistry 9 publications, 1.39%
Synthesis	Synthesis, 9, 1.39% Synthesis 9 publications, 1.39%
Nature Communications	Nature Communications, 8, 1.24% Nature Communications 8 publications, 1.24%
ACS Central Science	ACS Central Science, 8, 1.24% ACS Central Science 8 publications, 1.24%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 8, 1.24% Advanced Synthesis and Catalysis 8 publications, 1.24%
Chem	Chem, 7, 1.08% Chem 7 publications, 1.08%
Nature	Nature, 6, 0.93% Nature 6 publications, 0.93%
Synlett	Synlett, 6, 0.93% Synlett 6 publications, 0.93%
Dalton Transactions	Dalton Transactions, 6, 0.93% Dalton Transactions 6 publications, 0.93%
Science	Science, 6, 0.93% Science 6 publications, 0.93%
ACS Omega	ACS Omega, 5, 0.77% ACS Omega 5 publications, 0.77%
Journal of Catalysis	Journal of Catalysis, 4, 0.62% Journal of Catalysis 4 publications, 0.62%
Chemical Society Reviews	Chemical Society Reviews, 4, 0.62% Chemical Society Reviews 4 publications, 0.62%
Nature Catalysis	Nature Catalysis, 4, 0.62% Nature Catalysis 4 publications, 0.62%
Chinese Chemical Letters	Chinese Chemical Letters, 4, 0.62% Chinese Chemical Letters 4 publications, 0.62%
	10 20 30 40 50 60

Citations by publishers

	50 100 150 200 250
Wiley	Wiley, 224, 34.62% Wiley 224 publications, 34.62%
American Chemical Society (ACS)	American Chemical Society (ACS), 197, 30.45% American Chemical Society (ACS) 197 publications, 30.45%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 89, 13.76% Royal Society of Chemistry (RSC) 89 publications, 13.76%
Elsevier	Elsevier, 49, 7.57% Elsevier 49 publications, 7.57%
Springer Nature	Springer Nature, 36, 5.56% Springer Nature 36 publications, 5.56%
Thieme	Thieme, 16, 2.47% Thieme 16 publications, 2.47%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 7, 1.08% American Association for the Advancement of Science (AAAS) 7 publications, 1.08%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 6, 0.93% Multidisciplinary Digital Publishing Institute (MDPI) 6 publications, 0.93%
The Chemical Society of Japan	The Chemical Society of Japan, 5, 0.77% The Chemical Society of Japan 5 publications, 0.77%
Beilstein-Institut	Beilstein-Institut, 3, 0.46% Beilstein-Institut 3 publications, 0.46%
Pharmaceutical Society of Japan	Pharmaceutical Society of Japan, 2, 0.31% Pharmaceutical Society of Japan 2 publications, 0.31%
Taylor & Francis	Taylor & Francis, 2, 0.31% Taylor & Francis 2 publications, 0.31%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 2, 0.31% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 2 publications, 0.31%
Akademiai Kiado	Akademiai Kiado, 1, 0.15% Akademiai Kiado 1 publication, 0.15%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.15% Shanghai Institute of Organic Chemistry 1 publication, 0.15%
Society of Synthetic Organic Chemistry	Society of Synthetic Organic Chemistry, 1, 0.15% Society of Synthetic Organic Chemistry 1 publication, 0.15%
Cambridge University Press	Cambridge University Press, 1, 0.15% Cambridge University Press 1 publication, 0.15%
	50 100 150 200 250

We do not take into account publications without a DOI.
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Hartwig J. H. et al. Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities // ACS Central Science. 2016. Vol. 2. No. 5. pp. 281-292.

GOST all authors (up to 50) Copy

Hartwig J. H., Larsen M. A. Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities // ACS Central Science. 2016. Vol. 2. No. 5. pp. 281-292.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acscentsci.6b00032

UR - https://doi.org/10.1021/acscentsci.6b00032

TI - Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities

T2 - ACS Central Science

AU - Hartwig, John H

AU - Larsen, Matthew A

PY - 2016

DA - 2016/05/02 00:00:00

PB - American Chemical Society (ACS)

SP - 281-292

IS - 5

VL - 2

PMID - 27294201

SN - 2374-7943

SN - 2374-7951

ER -

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BibTex Copy

@article{2016_Hartwig,

author = {John H Hartwig and Matthew A Larsen},

title = {Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities},

journal = {ACS Central Science},

year = {2016},

volume = {2},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acscentsci.6b00032},

number = {5},

pages = {281--292},

doi = {10.1021/acscentsci.6b00032}

}

MLA

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MLA Copy

Hartwig, John H., et al. “Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities.” ACS Central Science, vol. 2, no. 5, May. 2016, pp. 281-292. https://doi.org/10.1021/acscentsci.6b00032.

Found error?

Publisher

American Chemical Society (ACS)

Journal

ACS Central Science

Quartile SCImago

Quartile WOS

Impact factor

18.2

ISSN

23747943 (Print)
23747951 (Electronic)