Alkali Metal Catalysed Double Hydrophosphorylation of Nitriles and Alkynes. Issue 16 (16th April 2019)

• Record Type: Journal Article
• Authors: Banerjee, Indrani; Harinath, Adimulam; Panda, Tarun K.
• Is Part Of: European journal of inorganic chemistry. Issue 16(2019)
• Page Start: 2224
• Page End: 2230
• Publication Date: 2019-04-16
• Subjects: Alkynes -- Alkali metals -- Hydrophosphorylation -- Nitriles -- Phosphane ligands; Chemistry, Inorganic -- Periodicals; Organometallic chemistry -- Periodicals; Bioinorganic chemistry -- Periodicals; Solid state chemistry -- Periodicals; 546
• DOI: 10.1002/ejic.201900164
• Languages: English
• ISSNs: 1434-1948

Abstract

Abstract : Catalytic C–P and N–P bond formation via double hydrophosphorylation of nitriles with diphenylphosphane oxide using alkali metal precatalyst [MN(SiMe3 )2 ] (M = Li, Na, K) is reported. The potassium congener was observed to be the most efficient catalyst for converting aryl nitriles to the corresponding N‐((diphenyl‐phosphoryl)(aryl)methyl)‐P, P‐diphenylphosphinic amide [ArCHP(O)‐Ph2 NHP(O)Ph2 ] at mild temperature (60 °C) and with neat reactants. Double hydrophosphorylation of alkynes with HP(O)Ph2 is also very effective when [KN(SiMe3 )2 ] is used as a precatalyst at room temperature and gives the corresponding 1, 2‐diylbis(diphenyl‐phosphane oxide [RCHP(O)Ph2 CH2 P(O)Ph2 ] as the product. A wider substrate scope of both reactions is explored. Abstract : Double hydrophosphorylation of nitriles and terminal alkynes with diphenylphosphane oxide with high yield and chemoselectivity for the preparation of organophosphorus compounds using alkali metal salts [MN(SiMe3 )2 ] (M = Li, Na, K) as precatalysts under ambient conditions is reported.