Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 80, 2016
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
21 Jul 2016
Accepted
23 Aug 2016
First published
23 Aug 2016

Chem. Commun., 2016,52, 11885-11888
Article type
Communication

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

Social activity

Search articles by author

Spotlight

Advertisements