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Issue 26, 2017
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Tertiary amine self-catalyzed intramolecular Csp3–H functionalization with in situ generated allenes for the formation of 3-alkenyl indolines

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Abstract

A novel methodology for the synthesis of 3-alkenyl indolines through the reaction of in situ generated allenes with N-benzylic Csp3–H has been developed. The reaction was realized by Pd(0) catalyzed allenylation of propargyl carbonate with organoboron and subsequent tertiary amine self-catalyzed Csp3–H functionalization in a one-pot process. Control reactions suggested that the substrate itself might also serve as a Lewis base for the N-benzylic Csp3–H functionalization.

Graphical abstract: Tertiary amine self-catalyzed intramolecular Csp3–H functionalization with in situ generated allenes for the formation of 3-alkenyl indolines

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Publication details

The article was received on 01 Jan 2017, accepted on 09 Mar 2017 and first published on 09 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC00005G
Citation: Chem. Commun., 2017,53, 3721-3724
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    Tertiary amine self-catalyzed intramolecular Csp3–H functionalization with in situ generated allenes for the formation of 3-alkenyl indolines

    Y. Zhao, M. Xu, Z. Zheng, Y. Yuan and Y. Li, Chem. Commun., 2017, 53, 3721
    DOI: 10.1039/C7CC00005G

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