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Designing P‑Chirogenic 1,2-Diphosphinobenzenes at Both P‑Centers Using P(III)-Phosphinites

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journal contribution
posted on 31.05.2016, 17:35 by Jérôme Bayardon, Yoann Rousselin, Sylvain Jugé
A new enantiodivergent synthesis of P-chirogenic 1,2-diphosphinobenzenes (DP*B) bearing the chirality on one or both phosphorus centers is reported using aryne chemistry. The principle is based on successive reactions of 1,2-dibromobenzene with sec-phosphide boranes, then DABCO to remove the borane, and finally with chlorophosphines or P­(III)-chirogenic phosphinites. The efficiency of this synthesis was demonstrated by the stereoselective preparation of (S,S)-1,2-bis­(o-anisylphenylphosphino)­benzene. A compari­son of DIPAMP and homochiral DP*B ligands in asymmetric Rh- or Pd-catalyzed reactions was reported.