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. 2016 Apr 6;138(13):4302-5.
doi: 10.1021/jacs.6b00325. Epub 2016 Mar 23.

Selective Oxidation of an Active Intramolecular Amine/Borane Frustrated Lewis Pair with Dioxygen

Tongdao Wang  1 , Gerald Kehr  1 , Lei Liu  2 , Stefan Grimme  2 , Constantin G Daniliuc  1 , Gerhard Erker  1
Affiliations

Selective Oxidation of an Active Intramolecular Amine/Borane Frustrated Lewis Pair with Dioxygen

Tongdao Wang et al. J Am Chem Soc. .

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.

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