Aqueous rhodium-catalyzed hydroformylation of 1-decene in the presence of randomly methylated b-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 b-cyclodextrin (RAME-b-CD) has been studied by UV-
vis and NMR spectroscopies. Both ligands could be considered as non-interacting phosphines with
respect to RAME-b-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.