Literature DB >> 26998670

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

Tongdao Wang1, Gerald Kehr1, Lei Liu2, Stefan Grimme2, Constantin G Daniliuc1, Gerhard Erker1.   

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.

Entities:  

Year:  2016        PMID： 26998670     DOI： 10.1021/jacs.6b00325

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Reactivity of a coordinated inorganic acetylene unit, HBNH, and the azidoborane cation [HB(N3)].

Authors:  Anindya K Swarnakar; Christian Hering-Junghans; Michael J Ferguson; Robert McDonald; Eric Rivard
Journal:  Chem Sci       Date:  2016-12-19       Impact factor: 9.825

2.  CO/CO and NO/NO coupling at a hidden frustrated Lewis pair template.

Authors:  Tongdao Wang; Long Wang; Constantin G Daniliuc; Kamil Samigullin; Matthias Wagner; Gerald Kehr; Gerhard Erker
Journal:  Chem Sci       Date:  2017-01-04       Impact factor: 9.825

3.  Solid state frustrated Lewis pair chemistry.

Authors:  Long Wang; Gerald Kehr; Constantin G Daniliuc; Melanie Brinkkötter; Thomas Wiegand; Anna-Lena Wübker; Hellmut Eckert; Lei Liu; Jan Gerit Brandenburg; Stefan Grimme; Gerhard Erker
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825

4.  Proton to hydride umpolung at a phosphonium center via electron relay: a new strategy for main-group based water reduction.

Authors:  Takumi Oishi; Leonardo I Lugo-Fuentes; Yichuan Jing; J Oscar C Jimenez-Halla; Joaquín Barroso-Flores; Masaaki Nakamoto; Yohsuke Yamamoto; Nao Tsunoji; Rong Shang
Journal:  Chem Sci       Date:  2021-11-15       Impact factor: 9.825

5.  Exploring the Reactivity of B-Connected Carboranylphosphines in Frustrated Lewis Pair Chemistry: A New Frame for a Classic System.

Authors:  Jan Schulz; Menyhárt B Sárosi; Evamarie Hey-Hawkins
Journal:  Chemistry       Date:  2022-05-12       Impact factor: 5.020

6.  Activation of H-H, HO-H, C(sp2)-H, C(sp3)-H, and RO-H Bonds by Transition-Metal Frustrated Lewis Pairs Based on M/N (M = Rh, Ir) Couples.

Authors:  María Carmona; Roberto Pérez; Joaquina Ferrer; Ricardo Rodríguez; Vincenzo Passarelli; Fernando J Lahoz; Pilar García-Orduña; Daniel Carmona
Journal:  Inorg Chem       Date:  2022-08-10       Impact factor: 5.436
  6 in total

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