title: In situ phosphine oxide reduction: a catalytic Appel reaction.
abstract: Several important reactions in organic chemistry thrive on stoichiometric formation of phosphine oxides from phosphines. To avoid the resulting burden of waste and purification, cyclic phosphine oxides were evaluated for new catalytic reactions based on in situ regeneration. First, the ease of silane-mediated reduction of a range of cyclic phosphine oxides was explored. In addition, the compatibility of silanes with electrophilic halogen donors was determined for application in a catalytic Appel reaction based on in situ reduction of dibenzophosphole oxide. Under optimized conditions, alcohols were effectively converted to bromides or chlorides, thereby showing the relevance of new catalyst development and paving the way for broader application of organophosphorus catalysis by in situ reduction protocols.
authors: Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors: Henri A
authors: HA
authors: van Kalkeren
authors: Stefan H A M
authors: SH
authors: Leenders
authors: C Rianne A
authors: CR
authors: Hommersom
authors: Floris P J T
authors: FP
authors: Rutjes
authors: Floris L
authors: FL
authors: van Delft
mesh_terms: D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006842:Hydrocarbons, Brominated; D009943:Organophosphorus Compounds; D010087:Oxides; D010720:Phosphines