Literature DB >> 27027522

Highly Strained Heterocycles Constructed from Boron-Boron Multiple Bonds and Heavy Chalcogens.

Holger Braunschweig1, Philipp Constantinidis2, Theresa Dellermann3, William C Ewing3, Ingo Fischer2, Merlin Hess3, Fergus R Knight4, Anna Rempel3, Christoph Schneider3, Stefan Ullrich3, Alfredo Vargas5, J Derek Woollins4.   

Abstract

The reactions of a diborene with elemental selenium or tellurium are shown to afford a diboraselenirane or diboratellurirane, respectively. These reactions are reminiscent of the sequestration of subvalent oxygen and nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known between alkenes and the heavy chalcogens. Although carbon is too electronegative to affect the reduction of elements with lower relative electronegativity, the highly reducing nature of the B-B double bond enables reactions with Se(0) and Te(0) . The capacity of multiple bonds between boron atoms to donate electron density is highlighted in reactions where diborynes behave as nucleophiles, attacking one of the two Te atoms of diaryltellurides, forming salts consisting of diboratellurenium cations and aryltelluride anions.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; heterocycles; multiple bonds; selenium; tellurium

Year:  2016        PMID: 27027522     DOI: 10.1002/anie.201601691

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


  7 in total

1.  Easy access to nucleophilic boron through diborane to magnesium boryl metathesis.

Authors:  Anne-Frédérique Pécharman; Annie L Colebatch; Michael S Hill; Claire L McMullin; Mary F Mahon; Catherine Weetman
Journal:  Nat Commun       Date:  2017-04-07       Impact factor: 14.919

2.  Isolation of diborenes and their 90°-twisted diradical congeners.

Authors:  Julian Böhnke; Theresa Dellermann; Mehmet Ali Celik; Ivo Krummenacher; Rian D Dewhurst; Serhiy Demeshko; William C Ewing; Kai Hammond; Merlin Heß; Eckhard Bill; Eileen Welz; Merle I S Röhr; Roland Mitrić; Bernd Engels; Franc Meyer; Holger Braunschweig
Journal:  Nat Commun       Date:  2018-03-22       Impact factor: 14.919

3.  Mild synthesis of diboryldiborenes by diboration of B-B triple bonds.

Authors:  Tobias Brückner; Rian D Dewhurst; Theresa Dellermann; Marcel Müller; Holger Braunschweig
Journal:  Chem Sci       Date:  2019-06-11       Impact factor: 9.825

4.  cAAC-Stabilized 9,10-diboraanthracenes-Acenes with Open-Shell Singlet Biradical Ground States.

Authors:  Christian Saalfrank; Felipe Fantuzzi; Thomas Kupfer; Benedikt Ritschel; Kai Hammond; Ivo Krummenacher; Rüdiger Bertermann; Raphael Wirthensohn; Maik Finze; Paul Schmid; Volker Engel; Bernd Engels; Holger Braunschweig
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-25       Impact factor: 15.336

5.  π-Complexes of Diborynes with Main Group Atoms.

Authors:  William C Ewing; Theresa Dellermann; Y T Angel Wong; James D Mattock; Alfredo Vargas; David L Bryce; Rian D Dewhurst; Holger Braunschweig
Journal:  Chem Asian J       Date:  2020-04-16

6.  Attempts to Synthesize a Thiirane, Selenirane, and Thiirene by Dealkylation of Chalcogeniranium and Thiirenium Salts.

Authors:  Helmut Poleschner; Konrad Seppelt
Journal:  Chemistry       Date:  2020-10-22       Impact factor: 5.020

7.  Synthesis of Boron Analogues of Enamines via Hydroamination of a Boron-Boron Triple Bond.

Authors:  Tobias Brückner; Merlin Heß; Tom E Stennett; Anna Rempel; Holger Braunschweig
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-09       Impact factor: 16.823

  7 in total

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