高景星
新手性催化剂
个性化签名
- 姓名:高景星
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学术头衔:
博士生导师
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学科领域:
物理化学
- 研究兴趣:新手性催化剂
1942年5月生,1965年毕业于厦门大学化学系,现任化学系研究员。1983.11~1985.11公派在英国Southampton大学从事金属原子簇催化作用的访问研究。1995年4~8月和2000年7~11月应2001年度诺贝尔化学奖得主――日本名古屋大学野依良治(Ryoji Noyori)教授的两度邀请,作为访问教授先后在日本“新技术事业振兴团”、名古屋大学野依良治分子催化研究所开展学术交流和合作研究。1996年4月应邀作为访问教授在法国Rennes大学讲学。在国内外学术刊物发表论文九十多篇。研究成果“新手性催化剂的开发与应用”获国家发明专利 (专利号: ZL 97 1 12606.2;国际专利组分类号C07F 15/00)。近年来,开发了一类具有国际先进水平的手性氢化催化剂,得到国内外同行专家、包括2001年度诺贝尔化学奖得主野依良治教授的赞赏。多年来主持的研究项目“新手性配体、新手性催化剂的分子设计与在不对称催化中的应用”获中国高校自然科学成果二等奖(2001);参与“合成气制乙醇催化反应机理的研究”获国家教委科技进步一等奖一项(1995);是五项国家自然科学基金和福建省、教育部、厦门市重点课题基金等项目的主持人。
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469
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成果数
10
高景星, JING-XING GAO and HUI-LIN WAN, WAI-KWTOK WONG* and MAN-CHUNG TS, WING-TAK WONG
Polyhedron Vol. 15, No 8, pp. 1241-1251, 1996,-0001,():
-1年11月30日
The interaction of Ru(OAc)2(Ph3P)2 with one equivalent of N,N'-bis[o-(di-phenylphosphino) benzylidene]ethylenediamine (P2NzC2) in refluxing dichloromethanc gave trans-Ru(OAc)2(PzN2C2)'2H20 (I) in moderate yield (63%); in refluxing-toluene, it gave a red solid which upon recrystallization in CHC13 gave trans-RuC12(P2NzC2)" 2H20 (II) in good yield (92%). Compound II could also be prepared in good yield (85%) via the interaction of RuCI2(DMSO)4 with one equivalent of P2NzC2 in refluxing toluene. The interaction of RuCI2(DMSO)4 with one equivalent of N,N'-bis[o-(diphenylphosphino) benzylidene]- 1,3-diaminopropane (P2N2C3), N,N'-bis[o-(diphenylphosphino)benzyl] ethylenediamine (P2N2C2H4) and N,N'-bis[o-(diphenylphosphino)benzamido]ethane (P2N2C2-amide) in refluxing toluene gave trans-RuCl2(P2N2C3) (Ⅲ), trans-RuC12(P2N2C2H4) (IV) and trans-RuC12(P2N2C2-amide) (V) in good yield, respectively. The interaction of Fe(C104)2" 6H20 with one equivalent of P2N2C2 and P2N2C2H4 in refluxing acetonitrile gave trans-[Fe(P2N2C2)(CH3CN)2](CI04)2 (VI) and trans-[Fe(P2N2C2H4) (CH3CN)2](CIO4)2 (VII), respectively. Interaction of FeC12-4H20 with one equivalent of N,N'-bis[o-(diphenylphosphino)benzylidene]-l,6-diaminohexane (P2N2C6) in refluxing gave trans-FeC12(P2N2C6) (VIII). Complexes I-VIII have been fully characterized by ana-lytical and spectroscopic methods. The structure of IV has been established by an X-ray diffraction study. Compound II could be reduced to compound IV with NaBH4 in ethanol and oxidized to V with aqueous H202 acetonitrile. Catalytic studies showed that both Ⅱ and IV were effected catalysts for the hydrogenation of acrylic acid to propionic acid.
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【期刊论文】Preparation and Use of Polymersupported Chiral Ruthenium Complex Catalyst
高景星, Jing-Xing Oao*, Xiao Dong Yi, Chun-Liang Tang, Pian-Pian Xu and Hui-Lin Wan
Polym. Adv. TechnoL 12, 716 719 (2001),-0001,():
-1年11月30日
The chiral diiminodiphosphine ligand, [(R,R)-P2N2], has been prepared by the condensation of o-(diphenyl-phosphino)benzaldehyde and 1,2-diaminoeyclohexane. [(R,R)-P2N2] was reduced with excess NaBH4 in refluxing ethanol to afford the corresponding diaminodi-phosphine ligand [(R,R)-P2(NH)2]. The interaction of [(R,R)-P2(NH)2] with trans-RuCl2(DMSO)4 gave the chiral ruthenium complex [(R,R)-RuP2(NH)2] in 84% yield. The reaction of [(R,R)-RuP2(NH)2] with poly-(acrylic acid) using dieyclohexylcarbodiimine as the coupling agent, gave water soluble poly(acrylic acid salt)-supported chiral ruthenium complex [PAA-(R,R)-RuP2(NH)2]. These chiral ligands and ruthenium complexes have been fully characterized by microanalysis and IR, NMR spectroscopic methods. The polymer-bound ruthenium complex [PAA-(R,R)-RuP2(NH)2] as catalyst was used in asymmetric transfer hydrogenation of acetophenone in 2-propanol, producing the 1-phenyl-ethanol in 95% yield and 96% ee. The catalyst was reused twice with some loss of activity and enantioselec-tivity. Copyright
poly acrylic acid, chiral ruthenium complex, asymmetric catalysis, hydrogenation, ketone
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高景星, Jing-Xing Gao, ‡ Takao Ikariya, § and Ryoji Noyori*, §, |
Organometallics 1996, 15, 1087-1089,-0001,():
-1年11月30日
Summary: The trans-RuIICl2 complexes with structurally similar N,N¢-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine and N,N¢-bis[o-(diphenylphosphino)-benzyl]cyclohexane-1,2-diamine ligands have been synthesized, and their molecular structures have been determined. The C2-symmetric diphosphine/diaminebased Ru complex acts as an excellent catalyst precursor in asymmetric transfer hydrogenation of acetophenone in a 0.1 M 2-propanol solution, leading to 2-phenylethanol in 97% ee and in 93% yield after 7h at 45℃. This transfer hydrogenation is characterized by low reversibility under these conditions.
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高景星, Jing-Xing Gao a, *, Xiao-Dong Yi a, Pian-Pian Xu a, Chun-Liang Tang a, Hui-Lin Wan a, Takao Ikariya b
Journal of Organometallic Chemistry 592(1999)290-295,-0001,():
-1年11月30日
The new chiral ligands (S,S)-N,N%-bis[o-(diphenylphosphino)benzylidene]1,2-diiminocyclohexane, [(S,S)-1] and (S,S)-N,N%-bis[o-diphenylphosphino]benzyl-1,2-diaminocyclohexane, [(S,S)-2] have been prepared. The interaction of [(S,S)-1] and [(S,S)-2] with [Rh(COD)Cl]2 afforded the corresponding cationic rhodium complexes [(S,S)-3][X] and [(S,S)-4][X] (X PF6, BF4 or ClO4), respectively. [(S,S)-1], [(S,S)-2], [(S,S)-3][X] and [(S,S)-4][X] have been fully characterized by elemental analyses and spectroscopic methods. These chiral cationic rhodium complexes serve as catalytst precursors for the asymmetric transfer hydrogenation of acetophenone derivatives in 2-propanol and [(S,S)-4][PF6] acts as an excellent catalyst in the reduction of m-chloroacetophenone, giving the corresponding optical alcohols in 99% yield and up to 94% ee.
Chiral ligand, Chiral rhodium complexes, Transfer hydrogenation, Prochiral ketone, Asymmetric reduction
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【期刊论文】A new efficient chiral iridium catalyst for asymmetric transfer hydrogenation of ketones
高景星, Yan-Yun Li, Hui Zhang, Jian-Shan Chen, Xin-Li Liao, Zhen-Rong Dong, Jing-Xing Gao*
Journal of Molecular Catalysis A: Chemical 218(2004)153-156,-0001,():
-1年11月30日
The interaction of [Ir(COD)Cl]2 with chiral tetradentate diaminodiphosphine ligands gave chiral diaminodiphosphine-Ir(I) complexes, which were characterized by IR, NMR and CD. The new chiral iridium(I) complex catalysts were applied to asymmetric transfer hydrogenation of various aromatic ketones using 2-propanol as a source of hydrogen. The results showed that the corresponding chiral alcohols could be obtained with high activity (up to 99.4% yield) and excellent enantioselectivities (up to 99.0% ee) under mild conditions. Propiophenone was a preferred substrate with respect to catalytic activity and enantioselectivity in the presence of base. The catalytic turnover reached 4780mol product/mol iridium and the turnover frequency was as high as 1593h−1 at 55℃.
Chiral ligand, Chiral iridium complex, Asymmetric transfer hydrogenation, Aromatic ketone, Chiral alcohol
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高景星, Jing-Xing Gao a, ), Xiao-Dong Yi a, Pian-Pian Xu a, Chun-Liang Tang a, Hui Zhang a, Hui-Lin Wan a, Takao Ikariya b
Journal of Molecular Catalysis A: Chemical 159, 2000. 3-9,-0001,():
-1年11月30日
The interaction of [Rh(COD)Cl]2 with two equivalents of (S)-N,NX-biswo-( diphenylphosphino) benzylidenexpropane-1, 2-diamine [(S)-1] or (S)-N, N'-bis [o-(diphenylphosphino) benzylxpropane-1, 2-diamine [(S)-2] in benzene/methanol mixture and then precipitation by the addition of a solution of NH4PF6 in water afforded cationic rhodium (I) complexes [Rh(S)-MeP2N2] [PF6] and [Rh(S)-MeP2 (NH)2] [PF6] in good yield, respectively. Complexes [Rh(R,R)-C6P2N2] [PF6] and [Rh(R,R)-C6P2(NH)2] [PF6] were also prepared by an analogous manner. All these rhodium complexes have been characterized by analytical and spectroscopic methods and their asymmetric catalytic properties for enantioselective transfer hydrogenation of acetophenone have been tested. [Rh(R,R)-C6P2(NH)2] [PF6] was used as an excellent catalyst precursor for enantioselective transfer reduction of acetophenone in 2-propanol, leading to 2-phenylathanol in 97% yield and in 91% ee after 7 h at 83℃.
Cationic rhodium complexes, Enantioselective reduction, Simple ketones
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高景星, Jing-xing Gao a, ), Pian-pian Xu a, Xiao-dong Yi a, Chuan-bo Yang a, Hui Zhang a, Shou-heng Cheng a, Hui-lin Wan a, Khi-rui Tsai a, Takao Ikariya b
Journal of Molecular Catalysis A: Chemical 147, 1999. 105-111,-0001,():
-1年11月30日
The condensation of (S)-propane-1, 2-diamine with two equivalents of o- (diphenylphosphino) benzaldehyde gives (S)-N, N'-bis[o-(diphenylphosphino) benzylidenexpropane-1, 2-diaminew [(S)-1] ligand. The reduction of (S)-1 with excess NaBH4 is carried out in refluxing ethanol to afford corresponding (S)-N, N'-bis [o-(diphenylphosphino) benzylxpropane-1, 2-diamine [(S)-2]. The interaction of trans-RuCl2(DMSO)4 with one equivalent of (S)-1 or (S)-2 in refluxing toluene gives (S)-3 or (S)-4 in good yield, respectively. (S)-1, (S)-2, (S)-3 and (S)-4 have been fully characterized by analytical and spectroscopic methods. The structure of (R)-3 has been also established by an X-ray diffraction study. Catalytic studies showed that (S)-4 as an excellent catalyst precursor for the asymmetric transfer hydrogenation of acetophenone with 90% yield and up to 91% enantiomeric excess.
Chiral ligand, Ruthenium complex, Asymmetric transfer hydrogenation, Ketones
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【期刊论文】Hydrogenation and hydroformylation of olefins with water-soluble Ru 3(CO)9(TPPMS)3 catalyst
高景星, Jing-xing Gao*, Pian-pian Xu, Xiao-dong Yi, Hui-lin Wan, Khi-rui Tsai
Journal of Molecular Catalysis A: Chemical 147, 1999. 99-104,-0001,():
-1年11月30日
Water-soluble and air-stable triruthenium carbonyl cluster Ru3 CO.9 TPPMS.3 TPPMSssodium diphenylphosphi-nobenzene-m-sulphonate. was used as catalyst precursor to hydrogenated acrylic acid in good yield. The cluster also catalyzed the hydroformylation of propylene with syngas in water, the main product is n-butyraldehyde; side-products are iso-butyraldehyde and a small amount of 1-butyl and isobutyl alcohols. At 1208C and propylene, CO and H2 partial pressures of 0.7 MPa, 2.0 MPa and 2.0MPa, respectively, catalytic turnover of 61.2 mol productsrmol cluster h and product n:i ratio of 15.9 were obtained. For ethylene hydroformylation, the main product is propanal; side-products are 3-pentanone, 1-propanol and 2-methyl-pent-2-en-1-al. The catalyst was characterized before and after the reaction by IR and. X-ray photoelectron spectroscopy and the results were discussed as related to the possible catalytic active species. q1999 Elsevier Science B.V. All rights reserved.
Hydrogenation, Hydroformylation, Propylene, Ethylene, Water-soluble cluster catalyst
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【期刊论文】New Chiral Catalysts for Reduction of Ketones
高景星, JING-XING GAO, * HUI ZHANG, XIAO-DONG YI, PIAN-PIAN XU, CHUN-LIANG TANG, HUI-LIN WAN, KHI-RUI TSAI, AND TAKAO IKARIYA
CHIRALITY 12: 383-388 (2000),-0001,():
-1年11月30日
The condensation of o-(diphenylphosphino)benzaldehyde and various chiral diamine gives a series of diimino-diphosphine tetradentate ligands, which are reduced with excess NaBH4 in refluxing ethanol to afford the corresponding diaminodiphosphine ligands in good yield. The reactivity of these ligands toward trans-RuCl2(DMSO)4 and [Rh(COD)Cl]2 had been investigated and a number of chiral Ru(II) and Rh(I) complexes with the PNNP-type ligands were synthesized and characterized by microanalysis and IR, NMR spectroscopic methods. The chiral Ru(II) and Rh(I) complexes have proved to be excellent catalyst precursors for the asymmetric transfer hydrogenation of aromatic ketones, leading to optically active alcohols in up to 97% ee. Chirality 12: 383-388, 2000.
ruthenium, rhodium, chiral amino/, phosphine ligands, asymmetric catalysis, ketones, alcohols, enantioselective hydrogenations
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高景星, Hui Zhang, a Chuan-Bo Yang, a Yan-Yun Li, a Zhen-Rong Dong a, a Jing-Xing Gao, *a Hideaki Nakamura, b Kunihiko Murata b and Takao Ikariya*b
CHEM. COMMUN., 2003, 142-143,-0001,():
-1年11月30日
The chiral Ru cluster-based catalyst systems generated in situ from Ru3(CO)12 and chiral iiminodiphosphine tetradentate ligands effected asymmetric transfer hydrogenation of propiophenone in 2-propanol, leading to 1-phenyl-1-propanol in 94% yield and with 96% ee.
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