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<p>In this study, we report the synthesis and evaluation of three bisphosphine (<b>L1</b>–<b>L3</b>) and two monophosphine (<b>L4</b>, <b>L5</b>) ligands derived from a simple and cheap Bisphenol-A backbone for rhodium-catalysed hydroformylation of terminal alkenes in comparison with representative Xantphos and triphenylphosphine. All the ligands were characterised using NMR and HRMS analysis. Ligand <b>L3</b> with a rigid fluorene backbone displayed better performance than the other ligands in the rhodium-catalysed hydroformylation of 1-octene, giving &gt;99% conversion, 94% aldehyde selectivity with 74% linear selectivity and 566 turnover numbers. Scope extension with terminal alkenes varied with chain length and steric properties revealed the highest linear selectivity for 1-hexene (86%) and a deterioration in linear selectivity with the increase in alkyl chain length of the alkenes. 2,3-Dimethyl-2-butene and diisobutylene bearing a mixture of steric hindered terminal and internal alkenes showed poor conversions. Styrene showed the expected preference to branched aldehyde with 93% selectivity.</p> Graphical abstract <p>This work reported the detailed and systematic study of simple and cheap Bisphenol-A derived bisphosphine ligands in Rh-catalysed hydroformylation of terminal alkenes. The catalyst Rh/<b>L3</b> under optimised conditions gave excellent conversion (&gt;99%), excellent aldehyde selectivities (95–&gt;99%) and poor to good linear selectivities (70–86%) with up to 600 turnover numbers for aliphatic terminal alkenes.</p> <p></p>

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Exploring bisphenol-A derived bisphosphine ligands in Rh-catalysed hydroformylation of terminal alkenes

  • 期刊论文

  • 发表日期：

    2026年3月7日

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  • Sivadasan Dharani,
  • Muhammad Kamran,
  • Karuppathevan Ramki,
  • Salman Qadir,
  • Xinyu Ma,
  • Muhammad Sajjad,
  • Shao-Tao Bai

摘要

In this study, we report the synthesis and evaluation of three bisphosphine (L1–L3) and two monophosphine (L4, L5) ligands derived from a simple and cheap Bisphenol-A backbone for rhodium-catalysed hydroformylation of terminal alkenes in comparison with representative Xantphos and triphenylphosphine. All the ligands were characterised using NMR and HRMS analysis. Ligand L3 with a rigid fluorene backbone displayed better performance than the other ligands in the rhodium-catalysed hydroformylation of 1-octene, giving >99% conversion, 94% aldehyde selectivity with 74% linear selectivity and 566 turnover numbers. Scope extension with terminal alkenes varied with chain length and steric properties revealed the highest linear selectivity for 1-hexene (86%) and a deterioration in linear selectivity with the increase in alkyl chain length of the alkenes. 2,3-Dimethyl-2-butene and diisobutylene bearing a mixture of steric hindered terminal and internal alkenes showed poor conversions. Styrene showed the expected preference to branched aldehyde with 93% selectivity.

Graphical abstract

This work reported the detailed and systematic study of simple and cheap Bisphenol-A derived bisphosphine ligands in Rh-catalysed hydroformylation of terminal alkenes. The catalyst Rh/L3 under optimised conditions gave excellent conversion (>99%), excellent aldehyde selectivities (95–>99%) and poor to good linear selectivities (70–86%) with up to 600 turnover numbers for aliphatic terminal alkenes.