Journal of the American Chemical Society, volume 137, issue 8, pages 2958-2966

1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles

Sheng Xie ¹

Steven R. Lopez ²

Olof Ramström ¹

Mingdi Yan ^{1, 3}

K. N. Houk ²

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, KTH-Royal Institute of Technology, Teknikringen 36, Stockholm, Sweden |

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States |

Department of Chemistry, University of Massachusetts Lowell, Lowell, Massachusetts 01854, United States |

Publication type: Journal Article

Publication date: 2015-02-18

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/ja511457g

Copy DOI

PubMed ID: 25553488

General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAA–enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamine–azide cycloadditions.

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Chemistry Letters	Chemistry Letters, 1, 1.04% Chemistry Letters 1 publication, 1.04%
IUCrData	IUCrData, 1, 1.04% IUCrData 1 publication, 1.04%
Acta Crystallographica Section E: Crystallographic Communications	Acta Crystallographica Section E: Crystallographic Communications, 1, 1.04% Acta Crystallographica Section E: Crystallographic Communications 1 publication, 1.04%
Molecules	Molecules, 1, 1.04% Molecules 1 publication, 1.04%
Topics in Current Chemistry	Topics in Current Chemistry, 1, 1.04% Topics in Current Chemistry 1 publication, 1.04%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 1.04% Chemistry of Heterocyclic Compounds 1 publication, 1.04%
European Polymer Journal	European Polymer Journal, 1, 1.04% European Polymer Journal 1 publication, 1.04%
Tetrahedron	Tetrahedron, 1, 1.04% Tetrahedron 1 publication, 1.04%
Journal of Colloid and Interface Science	Journal of Colloid and Interface Science, 1, 1.04% Journal of Colloid and Interface Science 1 publication, 1.04%
Macromolecular Rapid Communications	Macromolecular Rapid Communications, 1, 1.04% Macromolecular Rapid Communications 1 publication, 1.04%
ChemistryOpen	ChemistryOpen, 1, 1.04% ChemistryOpen 1 publication, 1.04%
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Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.04% Advanced Synthesis and Catalysis 1 publication, 1.04%
	2 4 6 8 10

Citations by publishers

	5 10 15 20 25 30 35
American Chemical Society (ACS)	American Chemical Society (ACS), 33, 34.38% American Chemical Society (ACS) 33 publications, 34.38%
Wiley	Wiley, 25, 26.04% Wiley 25 publications, 26.04%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 15, 15.63% Royal Society of Chemistry (RSC) 15 publications, 15.63%
Elsevier	Elsevier, 8, 8.33% Elsevier 8 publications, 8.33%
Springer Nature	Springer Nature, 4, 4.17% Springer Nature 4 publications, 4.17%
International Union of Crystallography (IUCr)	International Union of Crystallography (IUCr), 2, 2.08% International Union of Crystallography (IUCr) 2 publications, 2.08%
Thieme	Thieme, 2, 2.08% Thieme 2 publications, 2.08%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 2, 2.08% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 2 publications, 2.08%
The Chemical Society of Japan	The Chemical Society of Japan, 1, 1.04% The Chemical Society of Japan 1 publication, 1.04%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 1.04% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 1.04%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 1, 1.04% American Association for the Advancement of Science (AAAS) 1 publication, 1.04%
Proceedings of the National Academy of Sciences (PNAS)	Proceedings of the National Academy of Sciences (PNAS), 1, 1.04% Proceedings of the National Academy of Sciences (PNAS) 1 publication, 1.04%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 1, 1.04% The Japan Institute of Heterocyclic Chemistry 1 publication, 1.04%
	5 10 15 20 25 30 35

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Xie S. et al. 1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles // Journal of the American Chemical Society. 2015. Vol. 137. No. 8. pp. 2958-2966.

GOST all authors (up to 50) Copy

Xie S., Lopez S. R., Ramström O., Yan M., Houk K. N. 1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles // Journal of the American Chemical Society. 2015. Vol. 137. No. 8. pp. 2958-2966.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/ja511457g

UR - https://doi.org/10.1021/ja511457g

TI - 1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles

T2 - Journal of the American Chemical Society

AU - Xie, Sheng

AU - Lopez, Steven R.

AU - Ramström, Olof

AU - Yan, Mingdi

AU - Houk, K. N.

PY - 2015

DA - 2015/02/18 00:00:00

PB - American Chemical Society (ACS)

SP - 2958-2966

IS - 8

VL - 137

PMID - 25553488

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

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BibTex Copy

@article{2015_Xie,

author = {Sheng Xie and Steven R. Lopez and Olof Ramström and Mingdi Yan and K. N. Houk},

title = {1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles},

journal = {Journal of the American Chemical Society},

year = {2015},

volume = {137},

publisher = {American Chemical Society (ACS)},

month = {feb},

url = {https://doi.org/10.1021/ja511457g},

number = {8},

pages = {2958--2966},

doi = {10.1021/ja511457g}

}

MLA

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MLA Copy

Xie, Sheng, et al. “1,3-Dipolar Cycloaddition Reactivities of Perfluorinated Aryl Azides with Enamines and Strained Dipolarophiles.” Journal of the American Chemical Society, vol. 137, no. 8, Feb. 2015, pp. 2958-2966. https://doi.org/10.1021/ja511457g.

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Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor

ISSN

00027863 (Print)
15205126 (Electronic)