Open Access

Nature Communications, volume 7, issue 1, publication number 10443

Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives

Shangda Li ¹

Lei Cai ¹

Huafang Ji ¹

Long Yang ¹

G. Li ^{1, 2}

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State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, China |

Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, CAS, China |

Publication type: Journal Article

Publication date: 2016-01-27

Springer Nature

Journal: Nature Communications

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 20411723, 20411723

DOI: 10.1038/ncomms10443

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PubMed ID: 26813919

General Chemistry

General Biochemistry, Genetics and Molecular Biology

General Physics and Astronomy

Abstract

Benzoic acids are highly important structural motifs in drug molecules and natural products. Selective C–H bond functionalization of benzoic acids will provide synthetically useful tools for step-economical organic synthesis. Although direct ortho-C–H functionalizations of benzoic acids or their derivatives have been intensely studied, the ability to activate meta-C–H bond of benzoic acids or their derivatives in a general manner via transition-metal catalysis has been largely unsuccessful. Although chelation-assisted meta-C–H functionalization of electron-rich arenes was reported, chelation-assisted meta-C–H activation of electron-poor arenes such as benzoic acid derivatives remains a formidable challenge. Herein, we report a general protocol for meta-C–H olefination of benzoic acid derivatives using a nitrile-based sulfonamide template. A broad range of benzoic acid derivatives are meta-selectively olefinated using molecular oxygen as the terminal oxidant. The meta-C–H acetoxylation, product of which is further transformed at the meta-position, is also reported. While directed ortho-metalation is a well-established protocol, meta-functionalisation of aromatic groups is more challenging. Here, the authors report a directed meta-C-H functionalisation of benzoic acid derivatives, using a nitrile-based sulfonamide directing group.

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Journal of the American Chemical Society	Journal of the American Chemical Society, 9, 5.59% Journal of the American Chemical Society 9 publications, 5.59%
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Nature Communications	Nature Communications, 4, 2.48% Nature Communications 4 publications, 2.48%
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Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 3, 1.86% Advanced Synthesis and Catalysis 3 publications, 1.86%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 3, 1.86% Organic and Biomolecular Chemistry 3 publications, 1.86%
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Chemistry Letters	Chemistry Letters, 1, 0.62% Chemistry Letters 1 publication, 0.62%
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Current Opinion in Green and Sustainable Chemistry	Current Opinion in Green and Sustainable Chemistry, 1, 0.62% Current Opinion in Green and Sustainable Chemistry 1 publication, 0.62%
Journal of Organometallic Chemistry	Journal of Organometallic Chemistry, 1, 0.62% Journal of Organometallic Chemistry 1 publication, 0.62%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 0.62% Coordination Chemistry Reviews 1 publication, 0.62%
Chinese Journal of Chemistry	Chinese Journal of Chemistry, 1, 0.62% Chinese Journal of Chemistry 1 publication, 0.62%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 1, 0.62% Asian Journal of Organic Chemistry 1 publication, 0.62%
Organometallics	Organometallics, 1, 0.62% Organometallics 1 publication, 0.62%
Chemistry of Materials	Chemistry of Materials, 1, 0.62% Chemistry of Materials 1 publication, 0.62%
	2 4 6 8 10 12 14 16 18

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	10 20 30 40 50 60
American Chemical Society (ACS)	American Chemical Society (ACS), 52, 32.3% American Chemical Society (ACS) 52 publications, 32.3%
Wiley	Wiley, 44, 27.33% Wiley 44 publications, 27.33%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 40, 24.84% Royal Society of Chemistry (RSC) 40 publications, 24.84%
Elsevier	Elsevier, 8, 4.97% Elsevier 8 publications, 4.97%
Springer Nature	Springer Nature, 6, 3.73% Springer Nature 6 publications, 3.73%
Thieme	Thieme, 3, 1.86% Thieme 3 publications, 1.86%
The Chemical Society of Japan	The Chemical Society of Japan, 1, 0.62% The Chemical Society of Japan 1 publication, 0.62%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.62% Shanghai Institute of Organic Chemistry 1 publication, 0.62%
Taylor & Francis	Taylor & Francis, 1, 0.62% Taylor & Francis 1 publication, 0.62%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 1, 0.62% American Association for the Advancement of Science (AAAS) 1 publication, 0.62%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.62% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.62%
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Li S. et al. Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives // Nature Communications. 2016. Vol. 7. No. 1. 10443

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Li S., Cai L., Ji H., Yang L., Li G. Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives // Nature Communications. 2016. Vol. 7. No. 1. 10443

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TY - JOUR

DO - 10.1038/ncomms10443

UR - https://www.nature.com/articles/ncomms10443

TI - Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives

T2 - Nature Communications

AU - Cai, Lei

AU - Li, Shangda

AU - Ji, Huafang

AU - Yang, Long

AU - Li, G.

PY - 2016

DA - 2016/01/27 00:00:00

PB - Springer Nature

IS - 1

VL - 7

PMID - 26813919

SN - 2041-1723

ER -

BibTex

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@article{2016_Li,

author = {Lei Cai and Shangda Li and Huafang Ji and Long Yang and G. Li},

title = {Pd(II)-catalysed meta-C–H functionalizations of benzoic acid derivatives},

journal = {Nature Communications},

year = {2016},

volume = {7},

publisher = {Springer Nature},

month = {jan},

url = {https://www.nature.com/articles/ncomms10443},

number = {1},

doi = {10.1038/ncomms10443}

}

Found error?

Publisher

Springer Nature

Journal

Nature Communications

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

20411723 (Print)
20411723 (Electronic)