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1998.9 - 2002.6 Nankai University, B. S.
2002.9 - 2007.6 Nankai University, SKLEOC, Ph. D.
N-Heterocyclic carbenes (NHCs) have attached much attention as a new family of ligands in the past decade. NHCs are known to form stronger bonds to late transition metals than phosphines since they are better σ-donors and possess less π-back donation capability than phosphines. Many functionalized NHC ligands , which have chelating atoms such as N, P, O, S et al., have been synthesized and their metal complexes are efficient catalysts for many reactions. The strong electron donation of NHCs increases the electron density of the metals and facilitates the oxidative addition with substrates. The high thermal stability of the metal complexes of NHCs are resistant to dissociation.
new type of rigid and bulky triaryl phosphine-functionalized dihydroimidazolium salts 64·HCl were synthesized and were used as ligands in palladium-catalyzed hydroarylation reaction for the first time. In the reaction of hydroarylation of indobenzene and norbornene, the catalysts were very efficient with high turnover numbers (TON, up to 4.6 × 105) and turnover frequencies (TOF, up to 2.4 × 104 h-1).
A phosphine-functionalized chiral dihydroimidazolium 65·HCl was synthesized from 2-naphthol and 2-naphthylamine. Chiral dihydroimidazolium 65·HCl was used in palladium-catalyzed asymmetric hydroarylation reaction of olefins with high efficiency and moderate level of enantioselectivity.
In addition, an asymmetric dimerization reaction of enamides catalyzed by chiral Brønsted acid was developed. Using this dimerization reaction a series of 1,3-diamine compounds with chiral quaternary carbons were conveniently constructed in high yield and up to 83% ee.
Keywords: N-heterocyclic carbenes, dihydoimidazolium salts, palladium, hydroarylation, organocatalysis, chiral Brønsted acid, enamide
1. Yi-Xia Jia, Jun Zhong, Shou-Fei Zhu, Can-Ming Zhang, Qi-Lin Zhou*, Chiral Βrønsted acid catalyzed enantioselective Friedel-Crafts reaction of indoles and α-aryl enamides: construction of chiral quaternary carbons, Angew. Chem. Int. Ed.2007, 46, 5565-5567.
2.Jun Zhong, Jian-Hua Xie, Ai-E Wang, Wei Zhang, Qi-Lin Zhou*, Highly efficient triaryl phosphine-functionalized N-heterocyclic carbene ligands for hydroarylation reaction, Synlett 2006, 1193-1196.
3.Ai-E Wang, Jun Zhong, Jian-Hua Xie, Kai Li, Qi-Lin Zhou*, Highly efficient Suzuki cross-coupling catalyzed by palladium/phosphine-imidazolium carbene system, Adv. Synth. Catal. 2004, 346, 595-598.