Journal
JOURNAL OF CO2 UTILIZATION
Volume 52, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.jcou.2021.101682
Keywords
Immobilized catalyst; Chiral dirhodium; Asymmetric cyclopropanation
Funding
- Deutsche Forschungsgemeinschaft [Bu-911/27-1]
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A novel immobilized chiral dirhodium catalyst has been prepared and shows high catalytic activity and significant enantioselectivity in asymmetric cyclopmpanation reaction. The catalyst can be readily recovered and reused.
A novel immobilized chiral dirhodium catalyst, Rh-2(5-PTTL)(3)(5-PITL-linker)- SBA-15 (8), has been prepared via click reaction of azide-groups on functionalized SBA-15 with the dirhodium complex Rh-2(S-PTTL)(3)(S-PTTL-alkyne) (6) containing an alkyne moiety. During the synthesis of this complex, one chiral ligand of the parent Rh-2(S-PTTL)(4) catalyst is exchanged with an analogous chiral ligand system containing an alkyne moiety, which to a great extent maintains the intrinsic catalytic performance of the catalyst. The heterogeneous dirhodium catalyst is characterized by FT-IR and C-13 solid-state NMR to validate the successful immobilization. The catalytic performance of the heterogeneous catalyst 8 is investigated in the asymmetric cyclopmpanation of 3-diazooxin-dole with different aryl alkenes that form spiro-cyclopropyloxindoles which serve as precursors for pharmaceuticals. The resulting heterogeneous catalyst shows high catalytic activity and significant enantioselectivity. Importantly, it can be readily recovered and reused at least four times without significant loss of its catalytic performance.
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