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Functionalized Pentafluoroethylphosphanes
Author(s) -
Allefeld Nadine,
Neumann Beate,
Stammler HansGeorg,
Ignat'ev Nikolai,
Hoge Berthold
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501733
Subject(s) - chemistry , aldehyde , stereocenter , hydrolysis , acetone , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , financial economics , economics
Bis(diethylamino)pentafluoroethylphosphane represents a versatile starting material for the synthesis of functionalized pentafluoroethylphosphanes. Perfluoroalkyl substituted aminophosphanes themselves already exhibit interesting coordination properties and were treated with the catalytically relevant salts PtCl 2 and PdCl 2 affording trans ‐[Cl 2 M{P(C 2 F 5 )(NEt 2 ) 2 } 2 ]. The hitherto unknown (C 2 F 5 )PBr 2 , accessible in good yields by treatment of C 2 F 5 P(NEt 2 ) 2 with HBr, was smoothly transformed into the corresponding phosphane, C 2 F 5 PH 2 , or fluoro derivative, C 2 F 5 PF 2 . Acidic hydrolysis of C 2 F 5 P(NEt 2 ) 2 yielded the phosphinic acid C 2 F 5 P(O)(OH)H, the anion of which was structurally characterized. The phosphinic acid smoothly adds to the carbonyl group of acetone under PC bond formation. An analogous reaction with aldehydes, for example, salicyl aldehyde, offers the possibility to generate stereocenters.