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Chelated Diborenes and their Inverse-Electron-Demand Diels- Alder Reactions with Dienes

Please always quote using this URN: urn:nbn:de:bvb:20-opus-178268
  • A doubly base-stabilized diborane based on a benzylphosphine linker was prepared by a salt elimination reaction between 2-LiC\(_6\)H\(_4\)CH\(_2\)PCy\(_2\).Et\(_2\)O and B\(_2\)Br\(_4\). This compound was reduced with KC8 to its corresponding diborene, with the benzylphosphine forming a five-membered chelate. The diborene reacts with butadiene, 2-trimethylsiloxy-1,3-butadiene and isoprene to form 4,5-diboracyclohexenes, which interconvert between their 1,1- (geminal) and 1,2- (vicinal) chelated isomers. The 1,1-chelated diborene undergoes aA doubly base-stabilized diborane based on a benzylphosphine linker was prepared by a salt elimination reaction between 2-LiC\(_6\)H\(_4\)CH\(_2\)PCy\(_2\).Et\(_2\)O and B\(_2\)Br\(_4\). This compound was reduced with KC8 to its corresponding diborene, with the benzylphosphine forming a five-membered chelate. The diborene reacts with butadiene, 2-trimethylsiloxy-1,3-butadiene and isoprene to form 4,5-diboracyclohexenes, which interconvert between their 1,1- (geminal) and 1,2- (vicinal) chelated isomers. The 1,1-chelated diborene undergoes a halide-catalysed isomerisation into its thermodynamically favoured 1,2-isomer, which undergoes Diels-Alder reactions more slowly than the kinetic product.show moreshow less

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Metadaten
Author: Tom Stennett, James Mattock, Leanne Pentecost, Alfredo Vargas, Holger Braunschweig
URN:urn:nbn:de:bvb:20-opus-178268
Document Type:Preprint
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Angewandte Chemie, International Edition
Year of Completion:2018
Source:Angewandte Chemie, International Edition (2018) 57 (46), pp. 15276-15281. https://doi.org/10.1002/anie.201809217
DOI:https://doi.org/10.1002/anie.201809217
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie
Tag:DFT calculations; boron; chelates; cycloaddition; low-valent compounds
Release Date:2019/03/19
Note:
This is the pre-peer reviewed version of the following article: T. E. Stennett, J. D. Mattock, L. Pentecost, A. Vargas, H. Braunschweig, Angew. Chem. Int. Ed. 2018, 57, 15276., which has been published in final form at https://doi.org/10.1002/anie.201809217. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
EU-Project number / Contract (GA) number:669054
OpenAIRE:OpenAIRE
Licence (German):License LogoDeutsches Urheberrecht