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A nickel-catalyzed anti-carbometallative cyclization of alkyne–azides with organoboronic acids: synthesis of 2,3-diarylquinolines

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Abstract

An anti-carbonickelative cyclization via reversible alkenylnickel E/Z isomerization of 2-azido phenyl propargyl alcohols with aryl boronic acids is achieved using Ni(acac)2 as the catalyst to access 2,3-diaryl quinolines. It represents a rare example of trapping the vinyl metal intermediate with a nitrogen center, a non-carbon center electrophile.

Graphical abstract: A nickel-catalyzed anti-carbometallative cyclization of alkyne–azides with organoboronic acids: synthesis of 2,3-diarylquinolines

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Publication details

The article was received on 01 Nov 2017, accepted on 22 Dec 2017 and first published on 22 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08408K
Citation: Chem. Commun., 2018, Advance Article
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    A nickel-catalyzed anti-carbometallative cyclization of alkyne–azides with organoboronic acids: synthesis of 2,3-diarylquinolines

    G. Ranjith Kumar, R. Kumar, M. Rajesh and M. Sridhar Reddy, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC08408K

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