Literature DB >> 28004517

Selective Metal-free HB(C6 F5 )2 Catalyzed Allene Cyclotrimerization: Formation of 1,3,5-Trimethylenecyclohexane and Its Tris-hydroboration Product.

Xin Tao1, Gerald Kehr1, Constantin G Daniliuc1, Gerhard Erker1.   

Abstract

Allene is cyclotrimerized under metal-free conditions with the borane HB(C6 F5 )2 catalyst to selectively give 1,3,5-trimethylenecyclohexane (3 a). Three-fold hydroboration of the 1,3,5-cyclotrimer with Piers' borane gives the all-cis 1,3,5-CH2 B(C6 F5 )2 substituted cyclohexane product 14.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis acids; allenes; boron; cyclotrimerization; metal-free catalysis

Year:  2016        PMID： 28004517     DOI： 10.1002/anie.201610530

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Borane-induced ring closure reaction of oligomethylene-linked bis-allenes.

Authors:  Xin Tao; Karel Škoch; Constantin G Daniliuc; Gerald Kehr; Gerhard Erker
Journal:  Chem Sci       Date:  2019-12-18       Impact factor: 9.825

2.  HPCO-A Phosphorus-Containing Analogue of Isocyanic Acid.

Authors:  Alexander Hinz; René Labbow; Chris Rennick; Axel Schulz; Jose M Goicoechea
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-02       Impact factor: 15.336

3.  Halogenoborane mediated allene cyclooligomerization.

Authors:  Xin Tao; Christian Wölke; Constantin G Daniliuc; Gerald Kehr; Gerhard Erker
Journal:  Chem Sci       Date:  2019-01-02       Impact factor: 9.825

4.  Piers' Borane-Induced Tetramerization of Arylacetylenes.

Authors:  Max Hasenbeck; Tizian Müller; Arthur Averdunk; Jonathan Becker; Urs Gellrich
Journal:  Chemistry       Date:  2021-12-28       Impact factor: 5.020

5.  1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes.

Authors:  Arthur Averdunk; Max Hasenbeck; Tizian Müller; Jonathan Becker; Urs Gellrich
Journal:  Chemistry       Date:  2022-04-21       Impact factor: 5.020

6.  An Iron-Catalyzed Route to Dewar 1,3,5-Triphosphabenzene and Subsequent Reactivity.

Authors:  Adam N Barrett; Martin Diefenbach; Mary F Mahon; Vera Krewald; Ruth L Webster
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-09       Impact factor: 16.823
  6 in total

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