Due to high stability and recyclability of porous organic frameworks (POFs), the construction of POFs as robust asymmetric catalysts represents an important topic.1 Nevertheless, strategic design remains a challenging task due to limited cross-linking methods. Studies on binol derivatives as organocatalysts show that the binaphthyl backbone is expected to involve bulky substituents at 3 and 3’ positions.2 Carbazolic group seems well suited to provide steric hindrance and can be coupled under mild condition.3 Herein, we develop a novel chiral porous polymer based on carbazole and chiral binol (Bi-Cz-POF-1) as a highly active enantioselective catalyst. As a result, compared with homogenous counterpart, Bi-Cz-POF-1 exhibits higher enantioselectivity and better efficiency for asymmetric hydrogenation of 3-phenyl-2H-1,4-benzoxazine and 2-phenyl quinolone. The kinetic study that elucidates the promotion related with 3D-porous structure will also be discussed. Reference (1) Kundu, D. S.; Schmidt, J.; Bleschke, C.; Thomas, A.; Blechert, S. Angewandte Chemie International Edition 2012, 51, 5456. (2) Yamanaka, M.; Itoh, J.; Fuchibe, K.; Akiyama, T. Journal of the American Chemical Society 2007, 129, 6756. (3) Zhang, X.; Lu, J.; Zhang, J. Chemistry of Materials 2014, 26, 4023.

Chiral carbazolic porous framework as asymmetric heterogeneous organocatalyst

249th National Meeting (2015)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.