FLP-type alkenylation of a phosphafluorene
Phosphafluorenes, in which the chemically vulnerable C-9 position of the fluorene core has been replaced with phosphorus, demonstrate enhanced stability compared to conventional fluorene-based materials and belong to the general class of dibenzophospholes (DBPs). Phosphafluorene formation is commonly observed in the reductive functionalization of terphenyl-based dihalophosphanes. Here, we outline a high-yielding route towards phosphafluorene 1, starting from readily available <sup>Dipp</sup>TerPCl<sub>2</sub> (<sup>Dipp</sup>Ter = 2,6-Dipp-C<sub>6</sub>H<sub>3</sub>; Dipp = 2,6-iPr<sub>2</sub>-C<sub>6</sub>H<sub>3</sub>). Different functionalization strategies of 1 are outlined, including a complex with AuCl, its BH<sub>3</sub> adduct, and its corresponding sulphide. Interestingly, facile alkenylation of 1 was achieved in the presence of B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> and various phenylacetylene derivatives. This FLP-type alkenylation is <i>E</i>-selective giving zwitterionic phosphonium borates.
Authors
- Ayu Afiqah Nasrullah
- Tobias Taeufer (ORCID: https://orcid.org/0000-0002-1214-7283)
- Eszter Baráth (ORCID: https://orcid.org/0000-0001-8494-3388)
- Jola Pospech (ORCID: https://orcid.org/0000-0001-7794-2600)
- Christian Hering‐Junghans (ORCID: https://orcid.org/0000-0003-4937-2625)
Institutions
- Universiti of Malaysia Sabah (MY)
- Leibniz Institute for Catalysis (DE)
Publication Details
- Journal
- Dalton Transactions
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5dt01495f
- Primary Topic
- Synthesis and characterization of novel inorganic/organometallic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00