Planar-chiral imidazole-based phosphine ligands derived from [2.2]paracyclophane?

Dalton Transactions Pub Date: 2010-02-25 DOI: 10.1039/B923716J

Abstract

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.

Graphical abstract: Planar-chiral imidazole-based phosphine ligands derived from [2.2]paracyclophane
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