Tin(IV) bis(perfluoroalkanesulfonyl)amide complex as a highly selective Lewis acid catalyst for Baeyer-Villiger oxidation using hydrogen peroxide in a fluorous recyclable phase

被引:40
作者
Hao, XH [1 ]
Yamazaki, O [1 ]
Yoshida, A [1 ]
Nishikido, J [1 ]
机构
[1] Noguchi Inst, Itabashi Ku, Tokyo 1730003, Japan
关键词
Baeyer-Villiger oxidation; biphasic catalysis; hydrogen peroxide; perfluorinated ligand; tin;
D O I
10.1016/S0040-4039(03)01185-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sn[N(SO2C8F17)(2)](4) catalyst was shown to give an excellent yield and selectivity in a fluorous biphasic catalytic system for Baeyer-Villiger oxidation of cyclic ketones by 35% aqueous hydrogen peroxide, a green, safe and cheap oxidant. Furthermore, the catalyst was completely recovered and reused in the fluorous immobilized phase without loss of activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4977 / 4980
页数:4
相关论文
共 29 条
[11]  
FRISONE MD, 1993, ORGANOMETALLICS, V12, P148
[12]   Diphosphine-palladium and -platinum complexes as catalysts for the Baeyer-Villiger oxidation of ketones: Effect of the diphosphine, oxidation of acyclic ketones, and mechanistic studies [J].
Gavagnin, R ;
Cataldo, M ;
Pinna, F ;
Strukul, G .
ORGANOMETALLICS, 1998, 17 (04) :661-667
[13]  
GHOSEZ L, 2002, TETRAHEDRON S IN PRI, V58
[14]   Introduction - Fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond [J].
Gladysz, JA ;
Curran, DP .
TETRAHEDRON, 2002, 58 (20) :3823-3825
[15]   Recoverable catalysts. Ultimate goals, criteria of evaluation, and the green chemistry interface [J].
Gladysz, JA .
PURE AND APPLIED CHEMISTRY, 2001, 73 (08) :1319-1324
[16]   MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .133. METHYLTRIOXORHENIUM AS A CATALYST OF THE BAEYER-VILLIGER OXIDATION [J].
HERRMANN, WA ;
FISCHER, RW ;
CORREIA, JDG .
JOURNAL OF MOLECULAR CATALYSIS, 1994, 94 (02) :213-223
[17]   FACILE CATALYST SEPARATION WITHOUT WATER - FLUOROUS BIPHASE HYDROFORMYLATION OF OLEFINS [J].
HORVATH, IT ;
RABAI, J .
SCIENCE, 1994, 266 (5182) :72-75
[18]   Fluorous biphase chemistry [J].
Horváth, IT .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (10) :641-650
[19]   THE GAS-PHASE ACIDITIES OF VERY STRONG NEUTRAL BRONSTED ACIDS [J].
KOPPEL, IA ;
TAFT, RW ;
ANVIA, F ;
ZHU, SZ ;
HU, LQ ;
SUNG, KS ;
DESMARTEAU, DD ;
YAGUPOLSKII, LM ;
YAGUPOLSKII, YL ;
IGNATEV, NV ;
KONDRATENKO, NV ;
VOLKONSKII, AY ;
VLASOV, VM ;
NOTARIO, R ;
MARIA, PC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3047-3057
[20]   Lewis acid catalysis by lanthanide complexes with tris(perfluorooctanesulfonyl)methide ponytails in fluorous recyclable phase [J].
Mikami, K ;
Mikami, Y ;
Matsumoto, Y ;
Nishikido, J ;
Yamamoto, F ;
Nakajima, H .
TETRAHEDRON LETTERS, 2001, 42 (02) :289-292