Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

Glenn Burley; David L Davies; Gerry A Griffith; Michael Lee; Kuldip Singh

doi:10.1021/jo902466f

Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

Glenn Burley, David L Davies, Gerry A Griffith, Michael Lee, Kuldip Singh

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

66 Citations (Scopus)

Abstract

A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes.
Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive.We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.

Original language	English
Pages (from-to)	980-983
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	3
Early online date	4 Jan 2010
DOIs	https://doi.org/10.1021/jo902466f
Publication status	Published - 5 Feb 2010

Keywords

phase transfer solvent
microwave irradiation
bromoalkynes
N-alkynyl
N-bromoalkenyl heteroarenes

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10.1021/jo902466f

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New Molecular Tools For The 21st Century: Molecular Design Of New DNA-Based Devices
Burley, G.
EPSRC (Engineering and Physical Sciences Research Council)
1/04/12 → 31/03/13
Project: Research Fellowship

Cite this

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title = "Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium",

abstract = "A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive.We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.",

keywords = "phase transfer solvent, microwave irradiation , bromoalkynes, N-alkynyl , N-bromoalkenyl heteroarenes ",

author = "Glenn Burley and Davies, {David L} and Griffith, {Gerry A} and Michael Lee and Kuldip Singh",

year = "2010",

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doi = "10.1021/jo902466f",

language = "English",

volume = "75",

pages = "980--983",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

AU - Burley, Glenn

AU - Davies, David L

AU - Griffith, Gerry A

AU - Lee, Michael

AU - Singh, Kuldip

PY - 2010/2/5

Y1 - 2010/2/5

N2 - A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive.We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.

AB - A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes. Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive.We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.

KW - phase transfer solvent

KW - microwave irradiation

KW - bromoalkynes

KW - N-alkynyl

KW - N-bromoalkenyl heteroarenes

U2 - 10.1021/jo902466f

DO - 10.1021/jo902466f

M3 - Article

VL - 75

SP - 980

EP - 983

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -

Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

Abstract

Keywords

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New Molecular Tools For The 21st Century: Molecular Design Of New DNA-Based Devices

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