Air-stable trialkylphosphonium salts: simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes.
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]
Netherton
M R
MR
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Fu
G C
GC
D000388:Air; D002384:Catalysis; D010084:Oxidation-Reduction; D010720:Phosphines / Q000737:chemistry*
D010720:Phosphines