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9.14.5.1.1.1.1 Reaction of Primary Phosphines with Diynes

DOI: 10.1055/sos-SD-109-00525

Tobrman, T.Science of Synthesis Knowledge Updates, (20241134.

Since its discovery by Märkl and Potthast in 1967,[‌15‌] the direct reaction of 1,3-diynes with primary phosphines has been frequently used for the preparation of 1,2,5-trisubstituted 1H-phospholes (Scheme 3).[‌16‌‌19‌] The popularity of this procedure is associated with the availability of various 1,3-diynes.[‌20‌,‌21‌] In addition, the most commonly used phosphorus precursor (phenylphosphine) is commercially available or can be prepared by the reduction of dichloro(phenyl)phosphine with lithium aluminum hydride.[‌22‌] Typically, the reactions are carried out in a mixture of tetrahydrofuran and benzene,[‌16‌,‌17‌] or tetrahydrofuran and toluene.[‌18‌]

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