Manuscript_iedDielsAlder.pdf (802.66 kB)
Chelated diborenes and their inverse-electron-demand Diels-Alder reactions with dienes
journal contribution
posted on 2023-06-09, 15:09 authored by Tom Stennett, James D Mattock, Leanne Pentecost, Alfredo VargasAlfredo Vargas, Holger BraunschweigA doubly base-stabilized diborane based on a benzylphosphine linker was prepared by a salt elimination reaction between 2-LiC6H4CH2PCy2.Et2O and B2Br4. 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.
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Publication status
- Published
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- Published version
Journal
Angewandte Chemie International EditionISSN
1521-3773Publisher
WileyExternal DOI
Issue
46Volume
57Page range
15276-15281Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2018-09-20First Open Access (FOA) Date
2019-09-11First Compliant Deposit (FCD) Date
2018-09-20Usage metrics
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