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Bidentate Phosphines of Heteroarenes: 4,6‐Bis(diphenylphosphino)dibenzofuran and 4,6‐Bis(diphenylphosphino)dibenzothiophene
Author(s) -
Haenel Matthias W.,
Jakubik Dieter,
Rothenberger Eveline,
Schroth Gerhard
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240806
Subject(s) - dibenzofuran , dibenzothiophene , chemistry , tetramethylethylenediamine , medicinal chemistry , stereocenter , organic chemistry , denticity , catalysis , enantioselective synthesis , crystal structure
Twofold lithiation of dibenzofuran ( 6 ) and dibenzothiophene ( 12 ) with n ‐butyllithium/ N,N,N′,N′ ‐tetramethylethylenediamine (TMEDA) in n ‐hexane or n ‐pentane followed by the reaction with chlorodiphenylphosphine yielded the title compounds 4 and 5 , respectively, The monophosphines 4‐(diphenylphosphino)dibenzofuran ( 11 ) and 4‐(diphenylphosphino)dibenzothiophene ( 15 ) were obtained analogously via the monolithium compounds 9 and 14 of the heteroarenes. In the case of dibenzofuran ( 6 ), it was shown that mono‐ and dilithiation is controlled by temperature.