Reaction of Dihalodiboranes(4) with N-Heterocyclic Silylenes: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

Please always quote using this URN: urn:nbn:de:bvb:20-opus-153068
  • Dihalodiboranes(4) react with an N-heterocyclic silylene (NHSi) to generate NHSi-adducts of 1-aryl-2-silyl-1,2-diboraindanes as confirmed by X-ray crystallography, featuring the functionalization of both B–X (X = halogen) bonds and a C–H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl- 2,2-disilyldiborane(4) intermediates, generated by a two-fold B–X insertion, may be crucial for the C–H borylation that leads to the final products. Notably, our results demonstrate the first C–H borylation with aDihalodiboranes(4) react with an N-heterocyclic silylene (NHSi) to generate NHSi-adducts of 1-aryl-2-silyl-1,2-diboraindanes as confirmed by X-ray crystallography, featuring the functionalization of both B–X (X = halogen) bonds and a C–H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl- 2,2-disilyldiborane(4) intermediates, generated by a two-fold B–X insertion, may be crucial for the C–H borylation that leads to the final products. Notably, our results demonstrate the first C–H borylation with a strong B–F bond activated by silylene insertion.show moreshow less

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Author: Holger BraunschweigORCiD, Tobias Brückner, Andrea Deißenberger, Rian DewhurstORCiD, Annika Gackstatter, Annalena Gärtner, Alexander Hofmann, Thomas Kupfer, Dominic Prieschl, Torsten Thiess, Sunewang Rixin Wang
URN:urn:nbn:de:bvb:20-opus-153068
Document Type:Preprint
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Chemistry, A European Journal
Year of Completion:2017
Source:Chem. Eur. J. 2017, 23, 9491. DOI: 10.1002/chem.201702377
DOI:https://doi.org/10.1002/chem.201702377
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie
Tag:CH activation; bond activation; boron; borylation; diboraindanes; diborane; diboranes; silylenes; synthetic methods
Release Date:2017/09/07
Note:
This is the pre-peer reviewed version of the following article: H. Braunschweig, T. Brückner, A. Deißenberger, R. D. Dewhurst, A. Gackstatter, A. Gärtner, A. Hofmann, T. Kupfer, D. Prieschl, T. Thiess, S. R. Wang, Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes, Chem. Eur. J. 2017, 23, 9491., which has been published in final form at dx.doi.org/10.1002/chem.201702377. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving
EU-Project number / Contract (GA) number:669054
OpenAIRE:OpenAIRE
Licence (German):License LogoDeutsches Urheberrecht