Modular synthesis of benzo[b]phosphole derivatives via BuLi-mediated cyclization of (o-alkynylphenyl)phosphine.
Treatment of an (o-alkynylphenyl)phosphine with a stoichiometric amount of BuLi effects a cyclization reaction to produce a 3-lithiobenzo[b]phosphole, which affords a variety of 3-substituted benzophospholes upon reaction with electrophiles. An example is given for the synthesis of a bis-benzo[b]phosphole, which can be further converted to the corresponding benzo[b]phosphole oxide possessing high electron affinity.
Tsuji
Hayato
H
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo, Japan. tsuji@chem.a.u-tokyo.ac.jp
Sato
Kosuke
K
Ilies
Laurean
L
Itoh
Yoshimitsu
Y
Sato
Yoshiharu
Y
Nakamura
Eiichi
E
D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D009942:Organometallic Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*
D000480:Alkynes; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D010720:Phosphines; C434823:n-butyllithium