Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO2 to epoxides

doi:10.1016/S1872-2067(18)63023-2

Abstract

Abstract:

The catalytic synthesis of cyclic carbonates via the cycloaddition of CO₂ to epoxides is a standard methodology for CO₂ fixation. For this purpose, chiral basket-handle porphyrin-Co complexes were devised, prepared, and fully characterized by nuclear magnetic resonance, mass spectrometry, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, and specific rotation. The proposed metalloporphyrin catalysts were synthesized with either 1,1'-bi-2-naphthol or L-phenylalanine, which have different chirality, and then applied to the coupling of propylene oxide and CO₂ for generating chiral cyclic carbonates with good enantioselectivity under extremely mild conditions in the presence of tetrabutyl ammonium chloride as a co-catalyst. The good enantioselectivity in the cycloaddition reaction is attributed to a synergistic interplay between the chiral porphyrin catalysts and the substrate. The mechanism and enantioselectivity of the asymmetric cycloaddition reaction is discussed.

Key words: Carbon dioxide fixation, Chiral resolution, Cycloaddition, Epoxide, Chiral porphyrin-cobalt complex

Xiying Fu, Xinyao Jing, Lili Jin, Lilong Zhang, Xiaofeng Zhang, Bin Hu, Huanwang Jing. Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO₂ to epoxides[J]. Chinese Journal of Catalysis, 2018, 39(5): 997-1003.

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Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO₂ to epoxides

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