Journal of the American Chemical Society

, volume 127 , issue 1 , pages 210-216

Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates

Fahmi Himo ¹

Timothy Lovell ¹

Robert Hilgraf ¹

Vsevolod V Rostovtsev ¹

Louis Noodleman ¹

K. Barry Sharpless ¹

Valery V Fokin ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Contribution from the Department of Molecular Biology, and Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037 |

Publication type: Journal Article

Publication date: 2004-12-08

American Chemical Society (ACS)

Journal of the American Chemical Society

scimago Q1

wos Q1

SJR: 5.554

CiteScore: 22.5

Impact factor: 15.6

ISSN: 00027863, 15205126

DOI: 10.1021/ja0471525

Copy DOI

PubMed ID: 15631470

General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.

Found

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GOST |

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GOST Copy

Himo F. et al. Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates // Journal of the American Chemical Society. 2004. Vol. 127. No. 1. pp. 210-216.

GOST all authors (up to 50) Copy

Himo F., Lovell T., Hilgraf R., Rostovtsev V. V., Noodleman L., Sharpless K. B., Fokin V. V. Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates // Journal of the American Chemical Society. 2004. Vol. 127. No. 1. pp. 210-216.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/ja0471525

UR - https://doi.org/10.1021/ja0471525

TI - Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates

T2 - Journal of the American Chemical Society

AU - Himo, Fahmi

AU - Lovell, Timothy

AU - Hilgraf, Robert

AU - Rostovtsev, Vsevolod V

AU - Noodleman, Louis

AU - Sharpless, K. Barry

AU - Fokin, Valery V

PY - 2004

DA - 2004/12/08

PB - American Chemical Society (ACS)

SP - 210-216

IS - 1

VL - 127

PMID - 15631470

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2004_Himo,

author = {Fahmi Himo and Timothy Lovell and Robert Hilgraf and Vsevolod V Rostovtsev and Louis Noodleman and K. Barry Sharpless and Valery V Fokin},

title = {Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates},

journal = {Journal of the American Chemical Society},

year = {2004},

volume = {127},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/ja0471525},

number = {1},

pages = {210--216},

doi = {10.1021/ja0471525}

}

MLA

Cite this

MLA Copy

Himo, Fahmi, et al. “Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates.” Journal of the American Chemical Society, vol. 127, no. 1, Dec. 2004, pp. 210-216. https://doi.org/10.1021/ja0471525.

Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

scimago Q1

wos Q1

SJR

5.554

CiteScore

22.5

Impact factor

15.6

ISSN

00027863 (Print)

15205126 (Electronic)