page_title: Phosphenium
section_title: Reactions with dienes
hierarchical_section_title: Phosphenium / Reactivity / Reactions with dienes
caption_attribution_description: English: Hydroboration of pyridine catalyzed by NHP. adapted from https://pubs.acs.org/doi/abs/10.1021/jacs.7b09754
context_page_description: Phosphenium ions, not to be confused with phosphonium or phosphirenium, are divalent cations of phosphorus of the form [PR₂]⁺. Phosphenium ions have long been proposed as reaction intermediates.
context_section_description: Phosphenium intermediates are invoked as intermediates in the McCormack reaction, a method for the synthesis of organophosphorus heterocycles.  An illustrative reaction involves phenyldichlorophosphine and isoprene:
  Isolated phosphenium salts undergo this reaction readily.
  There are few examples of reactions catalyzed by phosphenium. In 2018, Rei Kinjo and coworkers reported the hydroboration of pyridines by the NHP salt, 1,3,2-diazaphosphenium triflate. The NHP is proposed to act as a hydride transfer reagent in this reaction.
caption: Hydroboration of pyridine catalyzed by NHP. adapted from ref.[13]
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