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New Strategies to Phosphino–Phosphonium Cations and Zwitterions
Author(s) -
Geier Stephen J.,
Dureen Meghan A.,
Ouyang Eva Y.,
Stephan Douglas W.
Publication year - 2010
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.200902369
Subject(s) - phosphonium , chemistry , heterolysis , medicinal chemistry , decomposition , zwitterion , thermal decomposition , phosphonium salt , salt (chemistry) , boron , stereochemistry , inorganic chemistry , polymer chemistry , organic chemistry , catalysis , molecule
By employing strategies based on frustrated Lewis pair chemistry, new routes to phosphino‐phosphonium cations and zwitterions have been developed. B(C 6 F 5 ) 3 is shown to react with H 2 and P 2 t Bu 4 to effect heterolytic hydrogen activation yielding the phosphino‐phosphonium borate salt [( t Bu 2 P)PH t Bu 2 ] [HB(C 6 F 5 ) 3 ] ( 1 ). Alternatively, alkenylphosphino‐phosphonium borate zwitterions are accessible by reaction of B(C 6 F 5 ) 3 and PhCCH with P 2 Ph 4 , P 4 Cy 4 , or P 5 Ph 5 affording the species [(Ph 2 P)P(Ph) 2 C(Ph)C(H)B(C 6 F 5 ) 3 ] ( 2 ), [(P 3 Cy 3 )P(Cy)C(Ph)C(H)B(C 6 F 5 ) 3 ] ( 3 ), and [(P 4 Ph 4 )P(Ph)C(Ph)C(H)B(C 6 F 5 ) 3 ] ( 4 ). A related phosphino‐phosphonium borate species—[(Ph 4 P 4 )P(Ph)C 6 F 4 B(F)(C 6 F 5 ) 2 ] ( 5 ) is also isolated from the thermolysis of B(C 6 F 5 ) 3 and P 5 Ph 5 .