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Iridium(I) Complexes of Upper Rim Functionalized PTA Derivatives. Synthesis, Characterization, and Use in Catalytic Hydrogenations (PTA = 1,3,5-Triaaza-7-phosphaadamantane)

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posted on 11.04.2011, 00:00 by Antonella Guerriero, Mikael Erlandsson, Andrea Ienco, Donald A. Krogstad, Maurizio Peruzzini, Gianna Reginato, Luca Gonsalvi
Reaction of (1,3,5-triaza-7-phosphaadamantane-6-yl)lithium (1; PTA-Li), synthesized in high yield and purity, with p-(dimethylamino)benzaldehyde gave the novel water-soluble β-phosphino alcohol (4′-(dimethylamino)phenyl)(1,3,5-triaza-7-phosphatricyclo[]dec-6-yl)methanol (2; PZA-NMe2). The oxide OPZA-NMe2 (3) and sulfide SPZA-NMe2 (4) were also obtained. Ir(I) complexes of (SR,RS)-PZA-NMe2 and the analogue phenyl(1,3,5-triaza-7-phosphatricyclo[]dec-6-yl)methanol (PZA) were obtained and used as precatalysts for the hydrogenation of α,β-unsaturated aldehydes and ketones and acetophenone using different mild reduction protocols. The X-ray crystal structure of the SR,RS diastereoisomer of PZA-NMe2 was also obtained and is described herein.