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Nature Communications, volume 9, issue 1, publication number 3343

Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp3)–H bonds

Xinxin Wu ¹

Hong Zhang ¹

Nana Tang ¹

Zhen Wu ¹

Dongping Wang ¹

Meishan Ji ¹

Yan Xu ¹

Min Wang ¹

Chen Zhu ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China |

Key Laboratory of Synthesis Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, China |

Publication type: Journal Article

Publication date: 2018-08-21

Springer Nature

Journal: Nature Communications

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 20411723, 20411723

DOI: 10.1038/s41467-018-05522-9

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General Chemistry

General Biochemistry, Genetics and Molecular Biology

General Physics and Astronomy

Abstract

Construction of C–C bonds via alkoxy radical-mediated remote C(sp3)–H functionalization is largely unexplored, as it is a formidable challenge to directly generate alkoxy radicals from alcohols due to the high bond dissociation energy (BDE) of O–H bonds. Disclosed herein is a practical and elusive metal-free alcohol-directed heteroarylation of remote unactivated C(sp3)–H bonds. Phenyliodine bis(trifluoroacetate) (PIFA) is used as the only reagent to enable the coupling of alcohols and heteroaryls. Alkoxy radicals are readily generated from free alcohols under the irradiation of visible light, which trigger the regioselective hydrogen-atom transfer (HAT). A wide range of functional groups are compatible with the mild reaction conditions. Two unactivated C–H bonds are cleaved and one new C–C bond is constructed during the reaction. This protocol provides an efficient strategy for the late-stage functionalization of alcohols and heteroaryls. Direct remote C–H functionalization of aliphatic alcohols via alkoxy radicals is largely unexplored. Here, the authors report the C(sp3)-heteroaryl bond formation in aliphatic alcohols mediated by alkoxy radicals formed with a hypervalent iodine reagent.

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Organic Letters	Organic Letters, 24, 14.55% Organic Letters 24 publications, 14.55%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 14, 8.48% Angewandte Chemie - International Edition 14 publications, 8.48%
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Organic Chemistry Frontiers	Organic Chemistry Frontiers, 10, 6.06% Organic Chemistry Frontiers 10 publications, 6.06%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 9, 5.45% Advanced Synthesis and Catalysis 9 publications, 5.45%
Journal of Organic Chemistry	Journal of Organic Chemistry, 8, 4.85% Journal of Organic Chemistry 8 publications, 4.85%
Journal of the American Chemical Society	Journal of the American Chemical Society, 6, 3.64% Journal of the American Chemical Society 6 publications, 3.64%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 6, 3.64% Organic and Biomolecular Chemistry 6 publications, 3.64%
Green Chemistry	Green Chemistry, 6, 3.64% Green Chemistry 6 publications, 3.64%
Chemical Science	Chemical Science, 6, 3.64% Chemical Science 6 publications, 3.64%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 5, 3.03% European Journal of Organic Chemistry 5 publications, 3.03%
Chemical Communications	Chemical Communications, 5, 3.03% Chemical Communications 5 publications, 3.03%
Chemical Reviews	Chemical Reviews, 4, 2.42% Chemical Reviews 4 publications, 2.42%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 4, 2.42% Chinese Journal of Organic Chemistry 4 publications, 2.42%
Chemical Society Reviews	Chemical Society Reviews, 4, 2.42% Chemical Society Reviews 4 publications, 2.42%
Nature Communications	Nature Communications, 4, 2.42% Nature Communications 4 publications, 2.42%
ChemSusChem	ChemSusChem, 3, 1.82% ChemSusChem 3 publications, 1.82%
ACS Catalysis	ACS Catalysis, 3, 1.82% ACS Catalysis 3 publications, 1.82%
Science China Chemistry	Science China Chemistry, 2, 1.21% Science China Chemistry 2 publications, 1.21%
Chem Catalysis	Chem Catalysis, 2, 1.21% Chem Catalysis 2 publications, 1.21%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 1.21% Chemistry - A European Journal 2 publications, 1.21%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 2, 1.21% Asian Journal of Organic Chemistry 2 publications, 1.21%
ACS applied materials & interfaces	ACS applied materials & interfaces, 2, 1.21% ACS applied materials & interfaces 2 publications, 1.21%
Synlett	Synlett, 2, 1.21% Synlett 2 publications, 1.21%
Current Organic Chemistry	Current Organic Chemistry, 1, 0.61% Current Organic Chemistry 1 publication, 0.61%
Chemical and Pharmaceutical Bulletin	Chemical and Pharmaceutical Bulletin, 1, 0.61% Chemical and Pharmaceutical Bulletin 1 publication, 0.61%
Trends in Chemistry	Trends in Chemistry, 1, 0.61% Trends in Chemistry 1 publication, 0.61%
Tetrahedron Chem	Tetrahedron Chem, 1, 0.61% Tetrahedron Chem 1 publication, 0.61%
iScience	iScience, 1, 0.61% iScience 1 publication, 0.61%
	5 10 15 20 25

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	10 20 30 40 50 60
Wiley	Wiley, 54, 32.73% Wiley 54 publications, 32.73%
American Chemical Society (ACS)	American Chemical Society (ACS), 48, 29.09% American Chemical Society (ACS) 48 publications, 29.09%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 37, 22.42% Royal Society of Chemistry (RSC) 37 publications, 22.42%
Elsevier	Elsevier, 8, 4.85% Elsevier 8 publications, 4.85%
Springer Nature	Springer Nature, 6, 3.64% Springer Nature 6 publications, 3.64%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 4, 2.42% Shanghai Institute of Organic Chemistry 4 publications, 2.42%
Thieme	Thieme, 3, 1.82% Thieme 3 publications, 1.82%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 2, 1.21% Multidisciplinary Digital Publishing Institute (MDPI) 2 publications, 1.21%
Bentham Science	Bentham Science, 1, 0.61% Bentham Science 1 publication, 0.61%
Pharmaceutical Society of Japan	Pharmaceutical Society of Japan, 1, 0.61% Pharmaceutical Society of Japan 1 publication, 0.61%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.61% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.61%
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Wu X. et al. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp3)–H bonds // Nature Communications. 2018. Vol. 9. No. 1. 3343

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Wu X., Zhang H., Tang N., Wu Z., Wang D., Ji M., Xu Y., Wang M., Zhu C. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp3)–H bonds // Nature Communications. 2018. Vol. 9. No. 1. 3343

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RIS Copy

TY - JOUR

DO - 10.1038/s41467-018-05522-9

UR - https://doi.org/10.1038/s41467-018-05522-9

TI - Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp3)–H bonds

T2 - Nature Communications

AU - Wu, Xinxin

AU - Zhang, Hong

AU - Tang, Nana

AU - Wu, Zhen

AU - Wang, Dongping

AU - Ji, Meishan

AU - Xu, Yan

AU - Wang, Min

AU - Zhu, Chen

PY - 2018

DA - 2018/08/21 00:00:00

PB - Springer Nature

IS - 1

VL - 9

SN - 2041-1723

ER -

BibTex

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BibTex Copy

@article{2018_Wu,

author = {Xinxin Wu and Hong Zhang and Nana Tang and Zhen Wu and Dongping Wang and Meishan Ji and Yan Xu and Min Wang and Chen Zhu},

title = {Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp3)–H bonds},

journal = {Nature Communications},

year = {2018},

volume = {9},

publisher = {Springer Nature},

month = {aug},

url = {https://doi.org/10.1038/s41467-018-05522-9},

number = {1},

doi = {10.1038/s41467-018-05522-9}

}

Found error?

Publisher

Springer Nature

Journal

Nature Communications

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

20411723 (Print)
20411723 (Electronic)