Open Access

Nature Communications, volume 10, issue 1, publication number 467

Visible light-induced direct α C–H functionalization of alcohols

Linbin Niu ¹

Jiamei Liu ¹

Xing An Liang ¹

Shengchun Wang ¹

Aiwen Lei ¹

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College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University, Wuhan, China |

Publication type: Journal Article

Publication date: 2019-01-28

Springer Nature

Journal: Nature Communications

Quartile SCImago

Quartile WOS

Impact factor: 16.6

ISSN: 20411723, 20411723

DOI: 10.1038/s41467-019-08413-9

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General Chemistry

General Biochemistry, Genetics and Molecular Biology

General Physics and Astronomy

Abstract

Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp3 C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp3 C–H alcohols. The observed reactivity may have significant implications for chemical transformations. Alcohols are very useful building blocks in organic synthesis, however C–H functionaliztion in presence of free –OH groups is highly challenging. Here, the authors report a selective visible light-promoted α-functionalization of free alcohols with heteroarenes mediated by Selectofluor.

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Citations by journals

	2 4 6 8 10 12 14
Organic Letters	Organic Letters, 14, 10.14% Organic Letters 14 publications, 10.14%
Journal of Organic Chemistry	Journal of Organic Chemistry, 13, 9.42% Journal of Organic Chemistry 13 publications, 9.42%
Green Chemistry	Green Chemistry, 11, 7.97% Green Chemistry 11 publications, 7.97%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 10, 7.25% Organic and Biomolecular Chemistry 10 publications, 7.25%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 6, 4.35% Advanced Synthesis and Catalysis 6 publications, 4.35%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 6, 4.35% European Journal of Organic Chemistry 6 publications, 4.35%
ACS Catalysis	ACS Catalysis, 6, 4.35% ACS Catalysis 6 publications, 4.35%
Chemical Communications	Chemical Communications, 6, 4.35% Chemical Communications 6 publications, 4.35%
Chemistry - A European Journal	Chemistry - A European Journal, 5, 3.62% Chemistry - A European Journal 5 publications, 3.62%
Chemical Science	Chemical Science, 5, 3.62% Chemical Science 5 publications, 3.62%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 4, 2.9% Angewandte Chemie - International Edition 4 publications, 2.9%
Angewandte Chemie	Angewandte Chemie, 4, 2.9% Angewandte Chemie 4 publications, 2.9%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 4, 2.9% Organic Chemistry Frontiers 4 publications, 2.9%
Nature Communications	Nature Communications, 3, 2.17% Nature Communications 3 publications, 2.17%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 3, 2.17% Asian Journal of Organic Chemistry 3 publications, 2.17%
Journal of the American Chemical Society	Journal of the American Chemical Society, 2, 1.45% Journal of the American Chemical Society 2 publications, 1.45%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 2, 1.45% Chinese Journal of Organic Chemistry 2 publications, 1.45%
ChemistrySelect	ChemistrySelect, 2, 1.45% ChemistrySelect 2 publications, 1.45%
Chinese Chemical Letters	Chinese Chemical Letters, 2, 1.45% Chinese Chemical Letters 2 publications, 1.45%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 2, 1.45% Chemistry - An Asian Journal 2 publications, 1.45%
Journal of Applied Physics	Journal of Applied Physics, 1, 0.72% Journal of Applied Physics 1 publication, 0.72%
Frontiers in Chemistry	Frontiers in Chemistry, 1, 0.72% Frontiers in Chemistry 1 publication, 0.72%
Journal of Chemical Sciences	Journal of Chemical Sciences, 1, 0.72% Journal of Chemical Sciences 1 publication, 0.72%
Molecular Catalysis	Molecular Catalysis, 1, 0.72% Molecular Catalysis 1 publication, 0.72%
Green Synthesis and Catalysis	Green Synthesis and Catalysis, 1, 0.72% Green Synthesis and Catalysis 1 publication, 0.72%
Journal of Photochemistry and Photobiology A: Chemistry	Journal of Photochemistry and Photobiology A: Chemistry, 1, 0.72% Journal of Photochemistry and Photobiology A: Chemistry 1 publication, 0.72%
Chem Catalysis	Chem Catalysis, 1, 0.72% Chem Catalysis 1 publication, 0.72%
Catalysis Communications	Catalysis Communications, 1, 0.72% Catalysis Communications 1 publication, 0.72%
Optical Materials	Optical Materials, 1, 0.72% Optical Materials 1 publication, 0.72%
	2 4 6 8 10 12 14

Citations by publishers

	5 10 15 20 25 30 35 40
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 39, 28.26% Royal Society of Chemistry (RSC) 39 publications, 28.26%
American Chemical Society (ACS)	American Chemical Society (ACS), 37, 26.81% American Chemical Society (ACS) 37 publications, 26.81%
Wiley	Wiley, 37, 26.81% Wiley 37 publications, 26.81%
Elsevier	Elsevier, 10, 7.25% Elsevier 10 publications, 7.25%
Springer Nature	Springer Nature, 5, 3.62% Springer Nature 5 publications, 3.62%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 2, 1.45% Shanghai Institute of Organic Chemistry 2 publications, 1.45%
American Institute of Physics (AIP)	American Institute of Physics (AIP), 1, 0.72% American Institute of Physics (AIP) 1 publication, 0.72%
Frontiers Media S.A.	Frontiers Media S.A., 1, 0.72% Frontiers Media S.A. 1 publication, 0.72%
Oxford University Press	Oxford University Press, 1, 0.72% Oxford University Press 1 publication, 0.72%
Walter de Gruyter	Walter de Gruyter, 1, 0.72% Walter de Gruyter 1 publication, 0.72%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 0.72% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 0.72%
Thieme	Thieme, 1, 0.72% Thieme 1 publication, 0.72%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.72% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.72%
	5 10 15 20 25 30 35 40

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Niu L. et al. Visible light-induced direct α C–H functionalization of alcohols // Nature Communications. 2019. Vol. 10. No. 1. 467

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Niu L., Liu J., Liang X. A., Wang S., Lei A. Visible light-induced direct α C–H functionalization of alcohols // Nature Communications. 2019. Vol. 10. No. 1. 467

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RIS Copy

TY - JOUR

DO - 10.1038/s41467-019-08413-9

UR - https://doi.org/10.1038/s41467-019-08413-9

TI - Visible light-induced direct α C–H functionalization of alcohols

T2 - Nature Communications

AU - Niu, Linbin

AU - Liu, Jiamei

AU - Liang, Xing An

AU - Wang, Shengchun

AU - Lei, Aiwen

PY - 2019

DA - 2019/01/28 00:00:00

PB - Springer Nature

IS - 1

VL - 10

SN - 2041-1723

ER -

BibTex

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BibTex Copy

@article{2019_Niu,

author = {Linbin Niu and Jiamei Liu and Xing An Liang and Shengchun Wang and Aiwen Lei},

title = {Visible light-induced direct α C–H functionalization of alcohols},

journal = {Nature Communications},

year = {2019},

volume = {10},

publisher = {Springer Nature},

month = {jan},

url = {https://doi.org/10.1038/s41467-019-08413-9},

number = {1},

doi = {10.1038/s41467-019-08413-9}

}

Found error?

Publisher

Springer Nature

Journal

Nature Communications

Quartile SCImago

Quartile WOS

Impact factor

16.6

ISSN

20411723 (Print)
20411723 (Electronic)