Catalytic Performance of Ruthenium-Supported Ionic-Liquid Catalysts in Sustainable Synthesis of Macrocyclic Lactones

被引:34
作者
Hagiwara, Hisahiro [1 ]
Nakamura, Tomomi [1 ]
Okunaka, Naotaro [1 ]
Hoshi, Takashi [2 ]
Suzuki, Toshio [2 ]
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Nishi Ku, Niigata 9502181, Japan
[2] Niigata Univ, Fac Engn, Nishi Ku, Niigata 9502181, Japan
基金
日本科学技术振兴机构;
关键词
OLEFIN-METATHESIS CATALYST; RING-CLOSING METATHESIS; CARBENE COMPLEX; RECYCLABLE CATALYST; SILICA-GEL; DIENE; POLYDIMETHYLSILOXANE; IMMOBILIZATION; IMIDAZOLIUM; PD(OAC)(2);
D O I
10.1002/hlca.200900334
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Thirteen- to eighteen-membered lactones were synthesized by ring-closing olefin-metathesis reactions of bis-olefins with heterogeneous Grubbs-supported ionic-liquid catalysts (SILCs), in which homogeneous Grubbs catalysts were confined in pores of alumina with the aid of an ionic liquid. The Grubbs-SILCs exhibited higher catalytic performance than their homogeneous counterparts and could be repeatedly recovered by simple filtration and re-used several times.
引用
收藏
页码:175 / 182
页数:8
相关论文
共 59 条
[1]   Well-Defined Silica-Supported Olefin Metathesis Catalysts [J].
Allen, Daryl P. ;
Van Wingerden, Matthew M. ;
Grubbs, Robert H. .
ORGANIC LETTERS, 2009, 11 (06) :1261-1264
[2]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[3]   An ionic liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids [J].
Audic, N ;
Clavier, H ;
Mauduit, M ;
Guillemin, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9248-9249
[4]   Polymer-Supported Well-Defined Metathesis Catalysts [J].
Buchmeiser, Michael R. .
CHEMICAL REVIEWS, 2009, 109 (02) :303-321
[5]   Ruthenium-catalyzed olefin metathesis in ionic liquids [J].
Buijsman, RC ;
van Vuuren, E ;
Sterrenburg, JG .
ORGANIC LETTERS, 2001, 3 (23) :3785-3787
[6]   Formation of medium-ring heterocycles by diene and enyne metathesis [J].
Chattopadhyay, Shital K. ;
Karmakar, Swastik ;
Biswas, Titas ;
Majumdar, K. C. ;
Rahaman, H. ;
Roy, B. .
TETRAHEDRON, 2007, 63 (19) :3919-3952
[7]   Olefin metathesis: The early days (Nobel lecture) [J].
Chauvin, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) :3740-3747
[8]   Novel imidazolium ion-tagged Ru-carbene complexes: synthesis and applications for olefin metathesis in ionic liquid [J].
Chen, Shu-Wei ;
Kim, Ju Hyun ;
Ryu, Ka Yeon ;
Lee, Won-Woong ;
Hong, Jongki ;
Lee, Sang-gi .
TETRAHEDRON, 2009, 65 (17) :3397-3403
[9]   α-Zirconium phosphonates: versatile supports for N-heterocyclic carbenes [J].
Chessa, Simona ;
Clayden, Nigel J. ;
Bochmann, Manfred ;
Wright, Joseph A. .
CHEMICAL COMMUNICATIONS, 2009, (07) :797-799
[10]   Ring-closing metathesis in biphasic BMI•PF6 ionic liquid/toluene medium:: a powerful recyclable and environmentally friendly process [J].
Clavier, H ;
Audic, N ;
Mauduit, M ;
Guillemin, JC .
CHEMICAL COMMUNICATIONS, 2004, (20) :2282-2283