title: Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.
abstract: Trialkylphosphines furnish unusual, sometimes unique, reactivity in a range of transformations. Unfortunately, their utility is compromised by their sensitivity to oxidation. We have examined a simple but powerful strategy for addressing this problem: convert air-sensitive trialkylphosphines into air-stable phosphonium salts via protonation on phosphorus. These robust salts serve as direct replacements for the corresponding phosphines (simple deprotonation under the reaction conditions by a Brønsted base liberates the trialkylphosphine) in a diverse set of applications. [reaction: see text]
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
authors.forename: M R
authors.initials: MR
authors.lastname: Netherton
authors.forename: G C
authors.initials: GC
authors.lastname: Fu
mesh_terms: D000388:Air; D002384:Catalysis; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry*
chemical_list: D010720:Phosphines