Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide

被引:142
作者
Csihony, S
Culkin, DA
Sentman, AC
Dove, AP
Waymouth, RM [1 ]
Hedrick, JL
机构
[1] Stanford Univ, Dept Chem, Ctr Polymer Interfaces & Macromol Assemblies, Stanford, CA 94305 USA
[2] IBM Almaden Res Ctr, San Jose, CA 95120 USA
关键词
D O I
10.1021/ja050909n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis and characterization of a series of primary and secondary alcohol adducts of 1,3-dimesitylimidazolin-2-ylidene is described. These adducts are stable as solids at room temperature, but readily release alcohol and the free carbene in solution. These alcohol adducts function as excellent single-component catalyst/initiators for the ring-opening polymerization of lactide under mild conditions, providing polymers with controlled molecular weights and narrow polydispersities. Multifunctional adducts were used to prepare poly(lactide)s of more complex architectures.
引用
收藏
页码:9079 / 9084
页数:6
相关论文
共 57 条
[1]   A STABLE DIAMINOCARBENE [J].
ARDUENGO, AJ ;
GOERLICH, JR ;
MARSHALL, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11027-11028
[2]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[3]  
Arduengo AJ, 1999, HELV CHIM ACTA, V82, P2348, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2348::AID-HLCA2348>3.0.CO
[4]  
2-M
[5]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[6]   Stable non-N-heterocyclic carbenes (non-NHC): recent progress [J].
Canac, Y ;
Soleilhavoup, M ;
Conejero, S ;
Bertrand, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :3857-3865
[7]   Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].
Chow, KYK ;
Bode, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127
[8]   First example of N-heterocyclic carbenes as catalysts for living polymerization:: Organocatalytic ring-opening polymerization of cyclic esters [J].
Connor, EF ;
Nyce, GW ;
Myers, M ;
Möck, A ;
Hedrick, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :914-915
[9]   Bredereck's reagent revisited: Latent anionic ring-opening polymerization and transesterification reactions [J].
Csihony, S ;
Beaudette, TT ;
Sentman, AC ;
Nyce, GW ;
Waymouth, RM ;
Hedrick, JL .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1081-1086
[10]   Controlled ring-opening polymerization of lactide and glycolide [J].
Dechy-Cabaret, O ;
Martin-Vaca, B ;
Bourissou, D .
CHEMICAL REVIEWS, 2004, 104 (12) :6147-6176