title: Amine-boranes bearing borane-incompatible functionalities: application to selective amine protection and surface functionalization.
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.
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. chandran@purdue.edu.
authors.forename: P
authors.initials: P
authors.lastname: Veeraraghavan Ramachandran
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. chandran@purdue.edu.
authors.forename: Ameya S
authors.initials: AS
authors.lastname: Kulkarni
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. chandran@purdue.edu.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA. chandran@purdue.edu.
authors.forename: Jianguo
authors.identifier: http://orcid.org/0000-0002-5743-2715
authors.initials: J
authors.lastname: Mei