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Compound <jats:bold>5<\/jats:bold> shows, at the same time, axial chirality and a sufficiently high energy barrier for internal rotation to prevent enantiomerization. Both enantiomers of <jats:bold>5<\/jats:bold> were isolated by means of chiral analytical HPLC, and their absolute configurations could be assigned by combining experimental data and DFT calculations. Despite its substitution pattern, <jats:bold>5<\/jats:bold> can still coordinate to transition\u2010metal centers through the lone pair of electrons on the phosphorus atom. Rapid C\uf8ffH activation on the adjacent aryl substituent at the 2\u2010position of the phosphorus heterocycle was achieved by using [{Cp*IrCl<jats:sub>2<\/jats:sub>}<jats:sub>2<\/jats:sub>] (Cp*=1,2,3,4,5\u2010pentamethylcyclopentadienyl) as a metal precursor. 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