Organic Letters, volume 13, issue 19, pages 5016-5019

Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions

Tao He ¹

Yu Lin ¹

Lei Zhang ¹

Lei Wang ¹

Min Wang ¹

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Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P.R. China, and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P.R. China

Huaibei Normal University

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Publication type: Journal Article

Publication date: 2011-08-29

American Chemical Society (ACS)

Journal: Organic Letters

Quartile SCImago

Quartile WOS

Impact factor: 5.2

ISSN: 15237060, 15237052

DOI: 10.1021/ol201779n

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A metal-free novel, simple, and highly efficient method for the direct C2-alkylation of azoles with alcohols and ethers has been developed on the basis of an oxidative C–H activation process. The dehydrogenative C–C cross-coupling reactions of α-position sp3 C–H in alcohols and ethers with the 2-position sp2 C–H in azoles proceeded smoothly in the presence of tert-butyl hydroperoxide (TBHP) under neat reaction conditions, which generated the corresponding products in good yields.

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ChemistrySelect	ChemistrySelect, 5, 2.54% ChemistrySelect 5 publications, 2.54%
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Angewandte Chemie	Angewandte Chemie, 5, 2.54% Angewandte Chemie 5 publications, 2.54%
Chemical Science	Chemical Science, 5, 2.54% Chemical Science 5 publications, 2.54%
Synlett	Synlett, 4, 2.03% Synlett 4 publications, 2.03%
Journal of the American Chemical Society	Journal of the American Chemical Society, 3, 1.52% Journal of the American Chemical Society 3 publications, 1.52%
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Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 2, 1.02% Chinese Journal of Organic Chemistry 2 publications, 1.02%
Nature Communications	Nature Communications, 2, 1.02% Nature Communications 2 publications, 1.02%
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Synthesis	Synthesis, 2, 1.02% Synthesis 2 publications, 1.02%
Beilstein Journal of Organic Chemistry	Beilstein Journal of Organic Chemistry, 1, 0.51% Beilstein Journal of Organic Chemistry 1 publication, 0.51%
Letters in Organic Chemistry	Letters in Organic Chemistry, 1, 0.51% Letters in Organic Chemistry 1 publication, 0.51%
Chemical Society Reviews	Chemical Society Reviews, 1, 0.51% Chemical Society Reviews 1 publication, 0.51%
Chinese Science Bulletin	Chinese Science Bulletin, 1, 0.51% Chinese Science Bulletin 1 publication, 0.51%
Transactions of Tianjin University	Transactions of Tianjin University, 1, 0.51% Transactions of Tianjin University 1 publication, 0.51%
Catalysis Communications	Catalysis Communications, 1, 0.51% Catalysis Communications 1 publication, 0.51%
	5 10 15 20 25

Citations by publishers

	10 20 30 40 50 60 70
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 62, 31.47% Royal Society of Chemistry (RSC) 62 publications, 31.47%
Wiley	Wiley, 48, 24.37% Wiley 48 publications, 24.37%
American Chemical Society (ACS)	American Chemical Society (ACS), 47, 23.86% American Chemical Society (ACS) 47 publications, 23.86%
Elsevier	Elsevier, 22, 11.17% Elsevier 22 publications, 11.17%
Thieme	Thieme, 6, 3.05% Thieme 6 publications, 3.05%
Springer Nature	Springer Nature, 3, 1.52% Springer Nature 3 publications, 1.52%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 2, 1.02% Shanghai Institute of Organic Chemistry 2 publications, 1.02%
Beilstein-Institut	Beilstein-Institut, 1, 0.51% Beilstein-Institut 1 publication, 0.51%
Bentham Science	Bentham Science, 1, 0.51% Bentham Science 1 publication, 0.51%
Tianjin Daxue/Tianjin University	Tianjin Daxue/Tianjin University, 1, 0.51% Tianjin Daxue/Tianjin University 1 publication, 0.51%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.51% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.51%
	10 20 30 40 50 60 70

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He T. et al. Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions // Organic Letters. 2011. Vol. 13. No. 19. pp. 5016-5019.

GOST all authors (up to 50) Copy

He T., Lin Yu., Zhang L., Wang L., Wang M. Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions // Organic Letters. 2011. Vol. 13. No. 19. pp. 5016-5019.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/ol201779n

UR - https://doi.org/10.1021/ol201779n

TI - Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions

T2 - Organic Letters

AU - Lin, Yu

AU - He, Tao

AU - Zhang, Lei

AU - Wang, Lei

AU - Wang, Min

PY - 2011

DA - 2011/08/29 00:00:00

PB - American Chemical Society (ACS)

SP - 5016-5019

IS - 19

VL - 13

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex Copy

@article{2011_He,

author = {Yu Lin and Tao He and Lei Zhang and Lei Wang and Min Wang},

title = {Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions},

journal = {Organic Letters},

year = {2011},

volume = {13},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/ol201779n},

number = {19},

pages = {5016--5019},

doi = {10.1021/ol201779n}

}

MLA

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MLA Copy

He, Tao, et al. “Direct C2-Alkylation of Azoles with Alcohols and Ethers through Dehydrogenative Cross-Coupling under Metal-Free Conditions.” Organic Letters, vol. 13, no. 19, Aug. 2011, pp. 5016-5019. https://doi.org/10.1021/ol201779n.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

Quartile SCImago

Quartile WOS

Impact factor

5.2

ISSN

15237060 (Print)
15237052 (Electronic)