Frustrated Lewis Pair Chemistry of Chiral (+)‐Camphor‐Based Aminoboranes. Issue 31 (20th June 2013)

• Record Type: Journal Article
• Authors: Lindqvist, Markus; Axenov, Kirill; Nieger, Martin; Räisänen, Minna; Leskelä, Markku; Repo, Timo
• Is Part Of: Chemistry. Volume 19:Issue 31(2013)
• Page Start: 10412
• Page End: 10418
• Publication Date: 2013-06-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201300462
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Dimethylamino‐(+)‐camphorenamine reacted with an equimolar amount of Piers' borane, HB(C₆F₅)₂, to give the corresponding iminium–hydroborate zwitterionic salt. Being in equilibrium with the parent enamine–HB(C₆F₅)₂ N–B pair, this salt was able to split hydrogen heterolytically, hydrogenating the iminium group in the molecule. Detailed studies revealed that the hydrogen splitting in this reaction proceeded through an intermolecular pathway leading to a bornylamine–HB(C₆F₅)₂ adduct. When the starting enamine is present in excess over HB(C₆F₅)₂, the produced bornylamine–HB(C₆F₅)₂ adduct breaks up, eliminating free bornylamine and forming the initial camphorenamine– HB(C₆F₅)₂ pair. This results in hydrogenation of the camphorenamine framework in a catalytic fashion.</p> </abstract>