Aqueous rhodium-catalyzed hydroformylation of 1-decene in the presence of randomly methylated β-cyclodextrin and 1,3,5-triaza-7-phosphaadamantane derivatives

The ability of PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) and its N-benzylated derivative (N-Bz-PTA)Cl to interact with the randomly methylated β-cyclodextrin (RAME-β-CD) has been studied by UV–vis and NMR spectroscopies. Both ligands could be considered as non-interacting phosphines with respect to RAME-β-CD. This has been turned to account in a rhodium-catalyzed hydroformylation reaction of 1-decene. A comparison with TPPTS (sodium salt of trisulfonated triphenylphosphine) highlights the beneficial effects of the PTA-based ligands on the chemoselectivity. Actually, chemoselectivities in aldehydes obtained with PTA and (N-Bz-PTA)Cl were very high (>98%) whatever the temperature. Moreover, contrary to what was observed with TPPTS, no decrease in regioselectivity was noticed as the linear to branched aldehydes ratio remains constant.

Both PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) and its N-benzylated derivative (N-Bz-PTA)Cl have been shown to be non-interacting phosphines towards the randomly methylated β-cyclodextrin. The consequences of this absence of interaction have been evaluated in an aqueous rhodium-catalyzed hydroformylation reaction of 1-decene. Beneficial effects of the PTA-based ligands on the chemoselectivity were demonstrated.Figure optionsDownload as PowerPoint slide