Open AccessBiphenylic Bisphosphines through ortho-Metalation of Aryldiphenylphosphine Oxides
Author(s) -
O. Desponds
Publication year - 1996
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1996.639
Subject(s) - phenyllithium , metalation , moiety , aryl , phosphine oxide , chemistry , group (periodic table) , medicinal chemistry , phosphine , halogenation , coupling reaction , stereochemistry , organic chemistry , alkyl , catalysis
Diphenyl-(2-trifluoromethyl)phosphine oxide was metalated next to the diphenylphosphinoyl group with LITMP. Upon iodination and Ullmann coupling, the corresponding 3,3'-disubstituted bis(phosphine oxide) was obtained. When phenyllithium was used as metalating agent, aryl/phenyl group exchange occurred. The torsional barrier for the planarization of the biaryl moiety was equal to 22 ± 1 kcal/mol.