title: Selective Oxidation of an Active Intramolecular Amine/Borane Frustrated Lewis Pair with Dioxygen.
abstract: Oxidation reactions are rarely encountered in frustrated Lewis pair (FLP) chemistry. We describe the selective reaction of an amine/borane FLP with molecular oxygen. The trimethylene-bridged amine/borane frustrated Lewis pair was prepared by hydroboration of N-allyl-tetramethylpiperidine with Piers' borane [HB(C6F5)2]. The intramolecular N/B system undergoes a variety of typical FLP reactions. It is a very active hydrogen splitting reagent at ambient conditions. Its reaction with dioxygen takes place rapidly at ambient conditions to give a tetrahydroisoxazolium/borate salt. A possible pathway of its formation is proposed and supported by DFT calculations.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Tongdao
authors.initials: T
authors.lastname: Wang
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Gerald
authors.initials: G
authors.lastname: Kehr
authors.affiliation: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn , Beringstrasse 4, 53115 Bonn, Germany.
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
authors.affiliation: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn , Beringstrasse 4, 53115 Bonn, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Grimme
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Constantin G
authors.initials: CG
authors.lastname: Daniliuc
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Erker