Planar-chiral imidazole-based phosphine ligands derived from  [2.2]paracyclophane.
Two planar chiral heteroaryl monophosphines have been synthesised and studied. The phosphines are readily prepared from 4-imidazole[2.2]paracyclophane by selective deprotonation and reaction with the appropriate dialkylchlorophosphines. The planar chiral imidazole was constructed in four steps from readily available [2.2]paracyclophane. The 2-phosphino-N-[2.2]paracyclophanes were active in the Suzuki-Miyaura coupling of aryl bromides and chlorides. Coordination studies indicate P,N-chelation in the solid-state. These studies lay the foundations for asymmetric couplings.
Seacome
Richard J
RJ
Department of Chemistry, University of Sussex, Falmer, UK BN1 9QJ.
Coles
Martyn P
MP
Glover
Jean E
JE
Hitchcock
Peter B
PB
Rowlands
Gareth J
GJ