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Rohde, Jan-Uwe
Transition Metal Chemistry
Research Interests
  • Inorganic chemistry, coordination chemistry, organometallic chemistry, chemical synthesis, catalysis, green chemistry, inorganic reaction mechanisms.

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Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water

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Title
Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
Author
Kim, Woo GyumKang, Mi EunLee, Jae BinJeon, Min HoLee, SungminLee, JunghaChoi, BongseoCal, Pedro M. S. D.Kang, SebyungKee, Jung-MinBernardes, Gonçalo J.L.Rohde, Jan-UweChoe, WonyoungHong, Sung You
Issue Date
201709
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.139, no.35, pp.12121 - 12124
Abstract
Transition-metal-catalyzed or metal-free azide–alkyne cycloadditions are versatile and indispensable synthetic methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been successfully applied to biomolecular reaction systems, the azide–alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a formidable challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a general synthetic method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is operationally simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are readily prepared via this nickel-catalyzed azide–alkyne cycloaddition.
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DOI
http://dx.doi.org/10.1021/jacs.7b06338
ISSN
0002-7863
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SNS_Journal Papers
SLS_Journal Papers
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