Co-reporter:Yu Jin, Yufeng Ji, Xiaojiang He, Suli Kan, Haidong Xia, Binqi Liang, Jia Chen, Hao Wu, Kai Guo and Zhenjiang Li
Polymer Chemistry 2014 vol. 5(Issue 8) pp:3098-3106
Publication Date(Web):28 Jan 2014
DOI:10.1039/C3PY01613G
o-Benzenedisulfonimide (OBS) was demonstrated for the first time to be a safe, recyclable, and water-tolerant Brønsted acidic catalyst for the ring-opening polymerization (ROP) of δ-valerolactone and ε-caprolactone using benzyl alcohol as the initiator. The polymerizations proceeded to afford poly(δ-valerolactone) and poly(ε-caprolactone) with controlled molecular weights and narrow polydispersities. The kinetics and chain extension experiments were carried out to confirm the controlled/living fashion of the polymerizations. In addition, 1H NMR and MALDI-TOF MS measurements strongly indicated that the initiator residue was incorporated into the obtained polymers. Furthermore, well-defined poly(δ-valerolactone)-block-poly(ε-caprolactone) has been successfully synthesized via OBS-catalyzed ROP.
Co-reporter:Meihong Jin;Guowei Song;Feng Zhou;Bo Fan ;Pingkai Ouyang
Journal of Heterocyclic Chemistry 2014 Volume 51( Issue 6) pp:1838-1843
Publication Date(Web):
DOI:10.1002/jhet.1113
2-Aryl-1-arylmethyl-1H-benzimidazoles were prepared in excellent yields by the condensation of o-phenylenediamine with aldehydes under mechanically activated solvent-free conditions in ball mill using FeCl3·6H2O as the catalyst.
Co-reporter:Xiaojiang He;Yufeng Ji;Yu Jin;Suli Kan;Haidong Xia;Jia Chen;Bingqi Liang;Hao Wu;Kai Guo
Journal of Polymer Science Part A: Polymer Chemistry 2014 Volume 52( Issue 7) pp:1009-1019
Publication Date(Web):
DOI:10.1002/pola.27082
ABSTRACT
The ring-opening polymerization (ROP) of trimethylene carbonate (TMC) using imidodiphosphoric acid (IDPA) as the organocatalyst and benzyl alcohol (BnOH) as the initiator has been investigated. The polymerization proceeded without decarboxylation to afford poly(trimethylene carbonate) (PTMiC) with controlled molecular weight and narrow polydispersity. 1H NMR, SEC, and MALDI-TOF MS measurements of the obtained PTMC clearly indicated the quantitative incorporation of the initiator at the chain end. The controlled/living nature for the IDPA-catalyzed ROP of TMC was confirmed by the kinetic and chain extension experiments. A bifunctional activation mechanism was proposed for IDPA catalysis based on NMR and FTIR studies. Additionally, 1,3-propanediol, 1,1,1-trimethylolpropane, and pentaerythritol were used as di-ol, tri-, and tetra-ol initiators, producing the telechelic or star-shaped polycarbonates with narrow polydispersity indices. The well-defined diblock copolymers, poly(trimethylene carbonate)-block-poly(δ-valerolactone) and poly(trimethylene carbonate)-block-poly(ε-caprolactone), have been successfully synthesized by using the IDPA catalysis system. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 1009–1019
Co-reporter:Suli Kan, Yu Jin, Xiaojiang He, Jia Chen, Hao Wu, Pingkai Ouyang, Kai Guo and Zhenjiang Li
Polymer Chemistry 2013 vol. 4(Issue 21) pp:5432-5439
Publication Date(Web):20 Jun 2013
DOI:10.1039/C3PY00667K
Imidodiphosphoric acid (IDPA) catalyzed ring-opening polymerization (ROP) of δ-valerolactone (δ-VL) and ε-caprolactone (ε-CL) with benzyl alcohol (BnOH) as the initiator in toluene at room temperature was investigated. The overall conversions of δ-VL and ε-CL to poly(δ-valerolactone) (PVL) and poly(ε-caprolactone) (PCL), respectively, were more than 90%. Experimental results indicated the living nature of the polymerizations. The polymerization reactions with different monomer-to-initiator ratios proceeded homogeneously to afford PVL and PCL with controlled molecular weight and narrow polydispersities. 1H NMR and MALDI-TOF MS measurements demonstrated the quantitative incorporation of the initiator in the polymer chains. The controlled/living character of the polymerization was examined thoroughly by the kinetics and chain extension experiments, indicating that the IDPA-catalyzed ROPs of δ-VL and ε-CL proceeded through a living mechanism.
Co-reporter:Jia Chen, Suli Kan, Haidong Xia, Feng Zhou, Xing Chen, Xiaoqin Jiang, Kai Guo, Zhenjiang Li
Polymer 2013 Volume 54(Issue 16) pp:4177-4182
Publication Date(Web):19 July 2013
DOI:10.1016/j.polymer.2013.05.069
The ring-opening polymerization (ROP) of trimethylene carbonate (TMC) catalyzed by phosphoramidic acid (PAA) and initiated with benzyl alcohol (BnOH) has been investigated. The polymerization conditions were optimized to afford well-defined polytrimethylene carbonates (PTMCs). The molecular weight of the obtained PTMC with the [TMC]0/[BnOH]0/[PAA]0 ratio of 40:1:1 was analyzed by 1H NMR, Mn = 4180 g mol−1, showed good agreement with that estimated from the initial ratio, Mn = 3830 g mol−1. The kinetics and chain extension experiments have been carried out to further justify the controlled/living nature of this polymerization. The 1H NMR, SEC, and MALDI-TOF MS measurements were applied to analyze the obtained PTMCs.
Co-reporter:Guowei Song, Meihong Jin, Zhenjiang Li and Pingkai Ouyang
Organic & Biomolecular Chemistry 2011 vol. 9(Issue 20) pp:7144-7150
Publication Date(Web):08 Jul 2011
DOI:10.1039/C1OB05848G
A practical procedure composed of an asymmetric Mannich-type reaction between N-tosyl imine and a Ni(II) complex of glycine with (R)-o-[N-(N-benzylprolyl)amino]bezaophenone (BPB) as a chiral auxiliary catalyzed by Et3N in DMF to (R,2R,3S)-complexes, and decomposition of products with HCl to offer syn-(2R,3S)-α,β-diamino acids, was developed. Stereochemical mechanism of the Mannich reaction was proposed and supported by determining the absolute configuration of the product of the Mannich reaction relying on X-ray analysis. This two-step approach to amino acids was a general method and adapted to large-scale preparation.
Co-reporter:Zhenjiang Li;Weisi Li;Yingjie Sun;He Huang ;Pingkai Ouyang
Journal of Heterocyclic Chemistry 2008 Volume 45( Issue 1) pp:285-288
Publication Date(Web):
DOI:10.1002/jhet.5570450135
Abstract
Amidosulfonic acid NH2–SO3H catalyzed direct condensations of o-phenylenediamines with α-diketones at room temperature in organic solvents to afford quinoxalines in excellent yields. The amidosulfonic acid as a solid acid catalyst in this preparation was efficient and recoverable.
Co-reporter:Zhenjiang Li, Xinghua Ren, Ping Wei, Honggui Wan, Yuhu Shi and Pingkai Ouyang
Green Chemistry 2006 vol. 8(Issue 5) pp:433-436
Publication Date(Web):03 Apr 2006
DOI:10.1039/B517864A
A facile synthesis of N-sulfonylimines by the condensation of aldehydes, sulfonylamide, and sodium arenesulfinate in the presence of sulfamic acid (NH2SO3H) in water–alcohol solvent and subsequent aqueous–biphasic basic elimination is reported.
Co-reporter:Guowei Song, Meihong Jin, Zhenjiang Li and Pingkai Ouyang
Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 20) pp:NaN7150-7150
Publication Date(Web):2011/07/08
DOI:10.1039/C1OB05848G
A practical procedure composed of an asymmetric Mannich-type reaction between N-tosyl imine and a Ni(II) complex of glycine with (R)-o-[N-(N-benzylprolyl)amino]bezaophenone (BPB) as a chiral auxiliary catalyzed by Et3N in DMF to (R,2R,3S)-complexes, and decomposition of products with HCl to offer syn-(2R,3S)-α,β-diamino acids, was developed. Stereochemical mechanism of the Mannich reaction was proposed and supported by determining the absolute configuration of the product of the Mannich reaction relying on X-ray analysis. This two-step approach to amino acids was a general method and adapted to large-scale preparation.