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Neutral Diboron Analogues of Archetypal Aromatic Species by Spontaneous Cycloaddition

Please always quote using this URN: urn:nbn:de:bvb:20-opus-138226
  • Among the numerous routes organic chemists have developed to synthesize benzene derivatives and heteroaro- matic compounds, transition-metal-catalyzed cycloaddition reactions are the most elegant. In contrast, cycloaddition reactions of heavier alkene and alkyne analogues, though limited in scope, proceed uncatalyzed. In this work we present the first spontaneous cycloaddition reactions of lighter alkene and alkyne analogues. Selective addition of unactivated alkynes to boron–boron multiple bonds under ambient con- ditions yielded diborocarbonAmong the numerous routes organic chemists have developed to synthesize benzene derivatives and heteroaro- matic compounds, transition-metal-catalyzed cycloaddition reactions are the most elegant. In contrast, cycloaddition reactions of heavier alkene and alkyne analogues, though limited in scope, proceed uncatalyzed. In this work we present the first spontaneous cycloaddition reactions of lighter alkene and alkyne analogues. Selective addition of unactivated alkynes to boron–boron multiple bonds under ambient con- ditions yielded diborocarbon equivalents of simple aromatic hydrocarbons, including the first neutral 6 π-aromatic dibora- benzene compound, a 2  π-aromatic triplet biradical 1,3-dibor- ete, and a phosphine-stabilized 2  π-homoaromatic 1,3-dihydro- 1,3-diborete. DFT calculations suggest that all three com- pounds are aromatic and show frontier molecular orbitals matching those of the related aromatic hydrocarbons, C\(_6\)H\(_6\) and C\(_4\)H\(_4\)\(^{2+}\), and homoaromatic C\(_4\)H\(_5\)\(^+\).show moreshow less
Metadaten
Author: Merle Arrowsmith, Julian Böhnke, Holger BraunschweigORCiD, Mehmet Celik, Christina Claes, William Ewing, Ivo Krummenacher, Katharina Lubitz, Christoph Schneider
URN:urn:nbn:de:bvb:20-opus-138226
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Angewandte Chemie, International Edition
Year of Completion:2016
Volume:55
Pagenumber:11271-11275
Source:Angewandte Chemie International Edition 2016, 55, 11271. doi:10.1002/anie.201602384
DOI:https://doi.org/10.1002/anie.201602384
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie
Tag:Aromaticity; Biradicals; Boron; Cycloaddition; Multiple bonds
Release Date:2017/10/24
EU-Project number / Contract (GA) number:669054
OpenAIRE:OpenAIRE
Note:
This is the peer reviewed version of the following article: Angew. Chem. Int. Ed. 2016, 55, 11271–11275, which has been published in final form at 10.1002/anie.201602384. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Licence (German):License LogoDeutsches Urheberrecht