University of Sussex
Browse
Manuscript_iedDielsAlder.pdf (802.66 kB)

Chelated diborenes and their inverse-electron-demand Diels-Alder reactions with dienes

Download (802.66 kB)
journal contribution
posted on 2023-06-09, 15:09 authored by Tom Stennett, James D Mattock, Leanne Pentecost, Alfredo VargasAlfredo Vargas, Holger Braunschweig
A 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.

History

Publication status

  • Published

File Version

  • Published version

Journal

Angewandte Chemie International Edition

ISSN

1521-3773

Publisher

Wiley

Issue

46

Volume

57

Page range

15276-15281

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2018-09-20

First Open Access (FOA) Date

2019-09-11

First Compliant Deposit (FCD) Date

2018-09-20

Usage metrics

    University of Sussex (Publications)

    Categories

    No categories selected

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC