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Issue 80, 2016
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Amine–boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization

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Abstract

The first general open-flask synthesis of amine–boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine–boranes represent stable molecules containing potentially incompatible electrophilic and nucleophilic centers in proximity. This convenient scalable synthesis provides a novel class of organic ligands for surface functionalization, as demonstrated by the formation of self-assembled layers of thiol- and alkoxysilane-bearing amine–boranes on gold and silica surfaces, respectively.

Graphical abstract: Amine–boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization

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Publication details

The article was received on 21 Jul 2016, accepted on 23 Aug 2016 and first published on 23 Aug 2016


Article type: Communication
DOI: 10.1039/C6CC06031E
Citation: Chem. Commun., 2016,52, 11885-11888
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    Amine–boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization

    P. Veeraraghavan Ramachandran, A. S. Kulkarni, Y. Zhao and J. Mei, Chem. Commun., 2016, 52, 11885
    DOI: 10.1039/C6CC06031E

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